2-Chloroethylamine hydrochloride → HCID 20433043, compound

HRID 2412340Notes

Reaction equation

HRID 2412340 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][OH:14])[CH:8]=[CH:9][CH:10]=1)[CH3:3].CC(C)([O-])C.[K+].Cl.Cl[CH2:23][CH2:24][NH2:25]>CN(C)C=O>[NH2:25][CH2:24][CH2:23][O:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 97937372-Chloroethylamine hydrochlorideHCID 19830911HCID 19830911, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20433043HCID 20433043, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-[(N,N-dimethylamino)methyl] benzene propanol (2.5 g), potassium tertiary butoxide (0.56 g), 2-chloroethylamine hydrochloride (0.59 g) in dimethylformamide (10 ml) was stirred at 0°-5° under a nitrogen atmosphere for 24 h. The mixture was poured onto water (1 1) and extracted with ethyl acetate. The organic extract was evaporated to leave a yellow oil which was purified by column chromatography using methanol followed by methanol: 0.880 ammonia; (20:1) to give the title compound as a brown oil (73 mg). T.l.c. system B Rf 0.2.

Workup

  1. additionThe mixture was poured onto water (1 1)
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. customwas evaporated
  5. customto leave a yellow oil which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8b5e912d4f2e4ac6888980b6559c7abc
Source dataset
uspto-grants-1985_01
Patent number
US04491586

Reaction notes

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