Hydrochloric Acid → HCID 86751315, compound

HRID 1379206Notes

Reaction equation

HRID 1379206 reaction equation
[ClH:1].[F:2][C:3]([F:61])([F:60])[C:4]1[CH:5]=[C:6]([CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:55]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][N:21](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:20][CH2:19]2)=[O:17])[CH2:11][C@H:10]1[CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=1)=[O:8].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[ClH:1].[ClH:1].[F:60][C:3]([F:2])([F:61])[C:4]1[CH:5]=[C:6]([CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:55]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[CH2:11][C@H:10]1[CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86751317HCID 86751317, compound

Product 1

HCID 86751315HCID 86751315, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4N hydrogen chloride in ethyl acetate solution (1.5 ml) was added dropwise to a solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-[(4-trityl-1-piperazinyl)carbonylmethyl]piperazine (480 mg) in ethyl acetate (5 ml) at 0° C. The resulting mixture was stirred at the same temperature for 1 hour and then allowed to stand overnight. Aqueous saturated sodium bicarbonate solution (20 ml) was added to the reaction mixture, and the product was extracted with ethyl acetate. The organic phase was washed with brine and dried. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (5:1) and treated with 4N hydrogen chloride in dioxane solution to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-[(1-piperazinyl)carbonylmethyl]piperazine dihydrochloride (250 mg).

Workup

  1. waitto stand overnight
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customdried
  5. customAfter evaporation of the solvent in vacuo
  6. customthe residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (5:1)
  7. additiontreated with 4N hydrogen chloride in dioxane solution

Sources & evidence

ORD record
ord-05aafd75a81a4bea9f1b35fa01234072
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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