Chapter 21: Amines. Organic derivatives of ammonia, NH

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247

C9H13NO [α]D +23°

13C NMR: 138.6, 129.1, 128.5, 126.3, 65.9, 54.2, 40.6

7.21-7.32 (m, 2H) 7.15-7.21 (m, 3H)

3.60 (1H, dd, J= 10.7, 4.1)

3.38 (1H, dd, J= 10.7, 7.0)

3.05-3.12 (1H, m)

2.77 (1H, dd, J= 13.3, 5.0)

2.49 (1H, dd, J= 13.3, 8.8)

2.35-2.45 (3H, br s)

IR:

248

Alkaloids: Naturally occurring compounds that contain a basic nitrogen atom

N

NCH3

nicotine

NH3C

CO2CH3

O Ph

Ococaine

O

HO

NCH3

HH

HO

morphine

NH

N

HO

H3CO

H

quinine

NH2

OCH3

H3CO

H3CO

mescaline

NH

coniine

N

NH

HO2C

H

CH3

lysergic acid

N

CH3

NCH3 CH3

OO

NHH3C

physostigmine

NH

OH

Histrionicotoxin

N

O

N

OH

H

H

H

strychnine

NH

NHO

MeO2C

NMeO

N

HOH

CO2CH3

O

O

RR= -CH3 vinblastineR= -CHO vincristine

CO2H

HONH2 N

H

NH2

tyrosine tryptophan

CO2H NH2

HO

HO

dopamine

HO

NH

NH2

serotonin

124

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