Triethylamine → HCID 22622664, compound

HRID 840168Notes

Reaction equation

HRID 840168 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[C:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)#[N:8].C(N(CC)CC)C>ClCCl>[C:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])=[O:14])=[CH:11][CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 22622664HCID 22622664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

100 mmol (9.2 ml) of 4-aminobutanol are slowly added, at a temperature of 5° C., to 100 mmol (16.56 g) of 4-cyanobenzoyl chloride in 400 ml of dichloromethane. While maintaining the temperature at 5° C., 100 mmol (13.9 ml) of triethylamine are added. The reaction mixture is stirred for 15 hours at room temperature before being hydrolysed. The organic phase is then decanted off and washed with a 1N hydrochloric acid solution. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel using a 97/3 dichloromethane/methanol mixture as eluant to yield the expected product.

Workup

  1. customThe organic phase is then decanted off
  2. washwashed with a 1N hydrochloric acid solution
  3. customAfter evaporating off the solvent
  4. customthe residue obtained
  5. customis purified by chromatography on silica gel using a 97/3 dichloromethane/methanol mixture as eluant

Sources & evidence

ORD record
ord-d628b668749646c6974b118804bce28c
Source dataset
uspto-grants-2002_04
Patent number
US06365605B1

Reaction notes

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