Triethylamine → HCID 178427913, compound

HRID 656330Notes

Reaction equation

HRID 656330 reaction equation
Cl.[OH:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1.[Cl:19][C:20]1[C:21]([CH3:30])=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C>C(#N)C>[Cl:19][C:20]1[C:21]([CH3:30])=[C:22]([S:26]([N:15]2[CH2:16][CH2:17][CH2:18][C@H:13]([C:11]([NH:10][C@H:7]3[CH2:6][CH2:5][C@H:4]([CH2:3][OH:2])[CH2:9][CH2:8]3)=[O:12])[CH2:14]2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 178479736HCID 178479736, compound

Product 1

HCID 178427913HCID 178427913, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (3S)-N-[trans-4-(hydroxymethyl)cyclohexyl]piperidine-3-carboxamide hydrochloride (170 mg, 0.61 mmol), 3-chloro-2-methylbenzenesulfonyl chloride (138 mg, 0.61 mmol), and triethylamine (0.21 mL, 1.54 mmol) in acetonitrile (3 mL) was stirred at r.t. for 2 hours. After removal of solvent, the residue was loaded on flash column with methylene chloride and eluted with ethyl acetate-hexane. 110 mg final product was obtained. (Yield: 41%). LCMS: m/z 429.0 (M+H)+; 879.2 (2M+Na)+.

Workup

  1. customAfter removal of solvent
  2. washeluted with ethyl acetate-hexane

Sources & evidence

ORD record
ord-3a451ce2f50d4fd6af43c3a593f93dc7
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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