Isobutyl chloroformate → HCID 14881413, compound

HRID 1460683Notes

Reaction equation

HRID 1460683 reaction equation
[C:1]1([CH:7]([NH2:30])[CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)=[O:18])[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:32]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[O:33]>C(Cl)(Cl)Cl>[C:1]1([CH:7]([NH:30][C:32]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[O:33])[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)=[O:18])[CH2:15][CH2:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 14099827HCID 14099827, compound

Product 1

HCID 14881413HCID 14881413, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 Grams of 6-[4-(4-phenyl-4-aminobutyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril was dissolved in 30 ml of chloroform, then to this solution was added 0.76 ml of isobutyl chloroformate at 0° C.-5° C. The reaction mixture was stirred at the same temperature for 3 hours, then concentrated. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =40:1), then converted into an oxalate by stirring with oxalic acid in acetone, and the oxalate was recrystallized from ethanol-water to yield 1.9 g of 6-[4-(4-phenyl-4-isobutoxycarbonylaminobutyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.oxalate. White powdery substance. Melting point: 221° C.-222° C.

Workup

  1. concentrationconcentrated
  2. customThe residue thus obtained
  3. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =40:1)
  4. stirringby stirring with oxalic acid in acetone
  5. customthe oxalate was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-8f080aa4794f41c2b101653b45d2cbb0
Source dataset
uspto-grants-1991_12
Patent number
US05071856

Reaction notes

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