4-Chlorobenzenesulfonyl chloride → HCID 53905327, compound

HRID 369072Notes

Reaction equation

HRID 369072 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[O:22][C:21]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=3[O:19][CH2:18]2)[CH2:12][CH2:11]1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][C:20]2[O:19][CH2:18][C@H:17]([CH2:16][N:13]3[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][S:35]([C:32]4[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=4)(=[O:37])=[O:36])[CH2:11][CH2:12]3)[O:22][C:21]=2[CH:23]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11000970HCID 11000970, compound

Product 1

HCID 53905327HCID 53905327, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.62 ml) was added to a solution of (S)-4-(aminomethyl)-1-(7-chloro-1,4-benzodioxan-2-ylmethyl)piperidine (0.44 g) and 4-chlorobenzene-sulphonyl chloride (0.62 g) in dichloromethane (22 ml), under nitrogen, and stirred for 20 hours. The reaction was diluted with dichloromethane (100 ml), washed with water (100 ml) and brine (100 ml), dried over anhydrous magnesium sulphate and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with a 20:1 mixture of dichloromethane and methanol gave (S)-(-)-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-4-chlorobenzene-sulphonamide as a white solid (0.30 g); m.p. 152-154° C., [α]D22.5 -23.8° (c=0.97, CH2Cl2).

Workup

  1. washwashed with water (100 ml) and brine (100 ml)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel eluting
  5. additionwith a 20:1 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-d12a1e4ccbc54282adc33e93cbc583d9
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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