Water → HCID 17848844, compound

HRID 1766003Notes

Reaction equation

HRID 1766003 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:7])[CH3:6].[Cl:19][CH2:20][CH2:21][C:22](Cl)=[O:23].O>ClC(Cl)C>[C:5]([N:8]1[C:14]2[CH:15]=[C:16]([C:22](=[O:23])[CH2:21][CH2:20][Cl:19])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11041530HCID 11041530, compound

Product 1

HCID 17848844HCID 17848844, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Aluminum chloride (30.8 g, 231 mmol) was added to a solution of 1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepine (17.5 g, 92.5 mmol) and 3-chloropropionyl chloride (13.2 ml, 139 mmol) in dichloroethane under cooling with water-bath, and then the mixture was stirred at 50° C. for 1 day. The reaction solution was poured into iced water and extracted with dichloromethane. The extract was washed with a saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1) and crystallized from hexane, whereby the title compound (8.47 g) was obtained as colorless powder with a mp. of 106 to 107° C.

Workup

  1. temperatureunder cooling with water-bath
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resultant residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1)
  7. customcrystallized from hexane, whereby the title compound (8.47 g)
  8. customwas obtained as colorless powder with a mp. of 106 to 107° C.

Sources & evidence

ORD record
ord-b42ac82317314103b0ef8498dd073ead
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

Loading…