4-Chlorobutyryl chloride → HCID 15292528, compound

HRID 1766024Notes

Reaction equation

HRID 1766024 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[Cl:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>[N+](C)([O-])=O>[C:5]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][Cl:19])=[CH:18][C:11]=2[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 193754873-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 15292528HCID 15292528, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Aluminum chloride (2.9 g, 21.7 mmol) was added little by little to a mixture of 3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2 g, 10.5 mmol) and 4-chlorobutyryl chloride (1.56 g, 11 mmol) in nitromethane (5 ml) at room temperature and stirred for 2 hours at room temperature. The reaction solution was poured into ice water which was then extracted with ethyl acetate, washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, whereby 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-chloro-1-butanone (2.9 g) was obtained.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with a saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-34ae7a6403824872b7527f321bd78ddf
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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