3-Amino-1-propanol → Bohemine

HRID 48183Notes

Reaction equation

HRID 48183 reaction equation
[CH2:1]([NH:8][C:9]1[N:17]=[C:16](Cl)[N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26]>>[OH:26][CH2:25][CH2:24][CH2:23][NH:22][C:16]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[CH:19]([CH3:21])[CH3:20])=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:17]=1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 10733091N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine

Product 1

HCID 2422BohemineYield 82%

Procedure

2-Chloroderivative (2) (0.5 mmol) and 3 ml of 3-aminopropanol were heated for 3 hours to 160° C. (sealed ampoule). Excess of the amine was evaporated at a temperature below 70° C. and the residue was purified by column chromatography (stepwise 0; 1; 2% MEOH in CHCl3) and crystallized from diethyl ether afforded the product in 82% yield; m.p. 98-101° C.

Workup

  1. customExcess of the amine was evaporated at a temperature below 70° C.
  2. customthe residue was purified by column chromatography (stepwise 0
  3. custom2% MEOH in CHCl3) and crystallized from diethyl ether
  4. customafforded the product in 82% yield

Sources & evidence

ORD record
ord-656827ec08e44cebadae73d5b22885ab
Source dataset
uspto-grants-2004_03
Patent number
US06703395B2

Reaction notes

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