1-Amino-2-propanol → HCID 22098528, compound

HRID 2260858Notes

Reaction equation

HRID 2260858 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH:10][CH:11]([CH3:14])[CH2:12][NH2:13].C(N(C(C)C)C(C)C)C>O>[OH:10][CH:11]([CH3:14])[CH2:12][NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 41-Amino-2-propanolHCID 145174-FluorobenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 22098528HCID 22098528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.1 g of 4-fluoro-benzonitrile, 7.5 g of 2-hydroxypropylamine and 17.4 ml of N-ethyl-diisopropylamine were heated together to 100° C. for 2.5 hours. The mixture was poured onto 250 ml of water, extracted five times with 50 ml of ethyl acetate and the combined organic phases were evaporated down. The product remaining was purified by column chromatography (silica gel; eluant: ethyl acetate) and crystallised by triturating with a 1:1-mixture of tert.butyl-methylether and petroleum ether.

Workup

  1. extractionextracted five times with 50 ml of ethyl acetate
  2. customthe combined organic phases were evaporated down
  3. customThe product remaining was purified by column chromatography (silica gel; eluant: ethyl acetate)
  4. customcrystallised
  5. customby triturating with a 1

Sources & evidence

ORD record
ord-778123f4c4444eafb33508204264327c
Source dataset
uspto-grants-1995_12
Patent number
US05478942

Reaction notes

Loading…