Triethylamine → HCID 53641702, compound

HRID 369071Notes

Reaction equation

HRID 369071 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.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[S:36](Cl)(=[O:38])=[O:37]>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:36]([C:30]4[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:29]=4[F:28])(=[O:38])=[O:37])[CH2:11][CH2:12]3)[O:22][C:21]=2[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 11000970HCID 11000970, compound

Product 1

HCID 53641702HCID 53641702, compoundYield 41.4%

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 2,6-difluorobenzene-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 to afford an orange oil. Purification by flash chromatography on silica gel eluting with a 20:1 mixture of dichloromethane and methanol gave an orange gum. Trituration with petroleum ether (b.p. 40-60° C.) yielded (S)-(-)-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-2,6-difluorobenzenesulphonamide as an off-white solid (0.29 g); m.p. 122-124° C., [α]D22.5 -22.1° (c=1.0, 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. customto afford an orange oil
  5. customPurification by flash chromatography on silica gel eluting
  6. additionwith a 20:1 mixture of dichloromethane and methanol
  7. customgave an orange gum

Sources & evidence

ORD record
ord-e82548ecd5f34cf7b599571afb4fc9f9
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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