Triethylamine → HCID 54134516, compound

HRID 369068Notes

Reaction equation

HRID 369068 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][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]([F: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 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 11000970HCID 11000970, compound

Product 1

HCID 54134516HCID 54134516, compoundYield 59.3%

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-fluorobenzenesulphonyl chloride (0.65 g) in dichloromethane (22 ml) under nitrogen and stirred for 3 hours. The reaction was left to stand for 14 hours then 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 19:1 mixture of dichloromethane and methanol gave a yellow oil which on trituration with diethyl ether yielded (S)-(-)-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-4-fluorobenzene-sulphonamide as a yellow solid (0.4 g); m.p. 127-129° C., [α]D22 -41.3° (c=0.72, MeOH).

Workup

  1. waitThe reaction was left
  2. waitto stand for 14 hours
  3. washwashed with water (100 ml) and brine (100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting
  7. additionwith a 19:1 mixture of dichloromethane and methanol
  8. customgave a yellow oil which on trituration with diethyl ether

Sources & evidence

ORD record
ord-9d32489df4314fd5baf8df1796a5f903
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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