Methyl chloroformate → HCID 20087994, compound

HRID 275360Notes

Reaction equation

HRID 275360 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=3)[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:11]2)[CH2:6][CH2:5]1.C([O-])([O-])=O.[K+].[K+].Cl[C:34]([O:36][CH3:37])=[O:35]>ClCCl>[CH3:37][O:36][C:34]([NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=3)[C:12]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[CH:11]2)[CH2:8][CH2:9]1)=[O:35]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 20087983HCID 20087983, compound

Product 1

HCID 20087994HCID 20087994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-[1-(2-aminoethyl)-4-piperidyl]-3-(4-fluorophenyl)-5-methyl-1H-indole 12a (8.9 g), K2CO3 (4.2 g) and dichloromethane (80 ml) was cooled to 0°-5° C. and a solution of methyl chloroformate (2.9 g)in dichloromethane (50 ml) was added during 15 min. After reaction for further 2 h at room temperature the reaction mixture was washed with water (2×50 ml), dried (MgSO4) and the solvents were evaporated in vacuo. This afforded the 1-[1-(N-methoxycarbonyl-2-aminoethyl)-4piperidyl]-3-(4-fluorophenyl)-5-methyl-1H-indole, as an oil, which was used without further purification. Yield: 8.8 g.

Workup

  1. temperaturewas cooled to 0°-5° C.
  2. customAfter reaction for further 2 h at room temperature the reaction mixture
  3. washwas washed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-2c5b76c6d9254e7eb138e5af758d7c59
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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