3-Chloropropionyl chloride → HCID 19375510, compound

HRID 2211127Notes

Reaction equation

HRID 2211127 reaction equation
Cl.[CH3:2][N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4]1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:18][CH2:19][CH2:20][C:21](Cl)=[O:22].[Na]>ClCCCl>[ClH:18].[CH3:2][N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][C:12]([C:21](=[O:22])[CH:20]=[CH2:19])=[CH:13][C:6]=2[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 693643-Chloropropionyl chlorideHCID 5360545SodiumHCID 6451240Aluminum(III) ChlorideHCID 19375516HCID 19375516, compound

Product 1

HCID 19375510HCID 19375510, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 30 ml of 1,2-dichloroethane, was dissolved 1.28 g of 3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride. To the solution were added, at room temperature, 2.1 g of aluminum chloride and 0.66 ml of 3-chloropropionyl chloride, then the mixture was stirred for 2 hours. The reaction mixture was poured into 50 ml of ice-water, then the pH of the aqueous solution was adjusted to not lower than 9 with a 40% aqueous solution of sodium hdyroxide, followed by extraction with 50 ml of dichloromethane. The organic layer was washed with 50 ml of pure water, which was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give an oily residue, which was crystallized from dichloromethane-ether to afford 0.83 g of the title compound as pale yellow crystals, m.p.120°-123° C.

Workup

  1. additionTo the solution were added, at room temperature
  2. extractionfollowed by extraction with 50 ml of dichloromethane
  3. washThe organic layer was washed with 50 ml of pure water, which
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto give an oily residue, which
  7. customwas crystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-5ac27269cd8843aa9ebd0213edb44088
Source dataset
uspto-grants-1995_10
Patent number
US05462934

Reaction notes

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