HCID 9916634, compound → HCID 9916635, compound

HRID 1937366Notes

Reaction equation

HRID 1937366 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C@@H:18]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[O:19][C:20]2[CH:36]=[CH:35][C:23]([C:24]([C:26]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][CH:27]=3)=[O:25])=[CH:22][CH:21]=2)[CH2:12][CH2:11]1>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C@@H:18]([C:37]2[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=2)[O:19][C:20]2[CH:36]=[CH:35][C:23]([C:24]([C:26]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][CH:27]=3)=[O:25])=[CH:22][CH:21]=2)[CH2:14][CH2:15]1

Participants

3

Reactant 1

HCID 9916634HCID 9916634, compound

Product 1

HCID 9916635HCID 9916635, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Separately, a suspension of (S)-3-[4-[3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propoxy]benzoyl]indole hydrochloride (2.0 g) in in methylene chloride was partitioned by addition of saturated sodium bicarbonate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from a solvent mixture of ethyl acetate and diisopropyl ether, to thereby obtain 1.4 g of (S)-3-[4-[3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propoxy]benzoyl]indole as light-yellow crystals.

Workup

  1. customwas partitioned by addition of saturated sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from a solvent mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-5dac8f35f75e4d20afe921784a0753cb
Source dataset
uspto-grants-2002_05
Patent number
US06395739B1

Reaction notes

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