Acetyl chloride → HCID 15487841, compound

HRID 1417851Notes

Reaction equation

HRID 1417851 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-21b113a08a9c4d0ea8d1c49944d2d116
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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