Acetyl chloride → HCID 15487841, compound

HRID 368869Notes

Reaction equation

HRID 368869 reaction equation
[C@H:1]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>CN(C=O)C>[C:36]([NH:28][S:25]([C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C@H:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:4][CH2:3][O:2]3)[CH2:14][CH2:15]2)=[CH:20][CH:21]=1)(=[O:27])=[O:26])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 133079Sonepiprazole

Product 1

HCID 15487841HCID 15487841, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-(-)-4-[4-[2-(Isochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide (EXAMPLE 49, 0.203 g) is stirred in DMF (2 ml) and triethylamine (0.211 ml) and acetyl chloride (0.108 ml) is added. The mixture is stirred at 20-25° for one hr and then at 50° for 4 days. After cooling, the mixture is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phases are dried over sodium sulfate, concentrated, and the residue is chromatographed (silica gel; ethyl acetate/dichloromethane (20/80)) to give the title compound after crystallization from methanol/dichloromethane/hexane, mp 160-161°; MS (m/z) 443; IR (mineral oil) 1593, 1157, 1094, 1136 and 1109 cm-1.

Workup

  1. waitat 50° for 4 days
  2. temperatureAfter cooling
  3. customthe mixture is partitioned between dichloromethane and aqueous sodium bicarbonate
  4. dry with materialThe organic phases are dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is chromatographed (silica gel; ethyl acetate/dichloromethane (20/80))

Sources & evidence

ORD record
ord-1b3cf75c08cf4f39a6d6cd4bc5770e29
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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