Water → HCID 86751324, compound

HRID 1379211Notes

Reaction equation

HRID 1379211 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]([F:41])([F:40])[C:12]1[CH:13]=[C:14]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]1[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:16].O>ClCCl>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:14]([CH:13]=[C:12]([C:11]([F:10])([F:40])[F:41])[CH:35]=1)[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:8](=[O:9])[NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:19][C@H:18]1[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 18502Cyclohexyl isocyanateHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

Product 1

HCID 86751324HCID 86751324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclohexyl isocyanate (0.06 ml) was added to a stirred solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.2 g) in dichloromethane (10 ml) at room temperature. After stirring for 4 hours, dichloromethane (10 ml) and water (5 ml) were added. The organic layer was separated, washed with brine and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (98:2) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-cyclohexylcarbamoyl-2-(1H-indol-3-yl-methyl)piperazine (0.18 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and methanol (98:2)

Sources & evidence

ORD record
ord-9a992c79c2cd433dba09bdeab95a0757
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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