Triethylamine → HCID 54463305, compound

HRID 369075Notes

Reaction equation

HRID 369075 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]([Br:27])[CH:25]=[CH:26][C:20]=3[O:19][CH2:18]2)[CH2:12][CH2:11]1.[Cl:28][C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[S:36](Cl)(=[O:38])=[O:37]>ClCCl>[Br: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:36]([C:30]4[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]=4[Cl:28])(=[O:38])=[O:37])[CH2:11][CH2:12]3)[O:22][C:21]=2[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 54221636HCID 54221636, compound

Product 1

HCID 54463305HCID 54463305, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.63 ml) was added to a solution of (S)-4-(aminomethyl)-1-(7-bromo-1,4-benzodioxan-2-ylmethyl)piperidine (0.5 g) and 2,3-dichlorobenzenesulphonyl chloride (0.74 g) in dichloromethane (15 ml) and stirred under nitrogen for 24 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 9:1 mixture of dichloromethane and methanol gave (S)-(-)-N-{[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-2,3-dichlorobenzensulphonamide as a cream solid (0.8 g) m.p. 93-95° C., [α]D22 -37.1°(c=0.93, MeOH).

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 9:1 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-7716a6aff3534ce9afbdb4711ce9d5e1
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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