Benzylamine → N-benzyl-3-piperidin-1-ylsulfonylbenzamide

HRID 1967492Notes

Reaction equation

HRID 1967492 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[N:25]1([S:31]([C:34]2[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=2)[C:37](O)=[O:38])(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl.ClCCl>[CH2:1]([NH:8][C:37](=[O:38])[C:36]1[CH:40]=[CH:41][CH:42]=[C:34]([S:31]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:33])=[O:32])[CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 7678893-(Piperidine-1-sulfonyl)benzoic acidHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 1076673N-benzyl-3-piperidin-1-ylsulfonylbenzamideYield 65.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Benzylamine (12 mg), triethylamine (0.047 mL) and 25% dichloromethane solution of 2-chloro-1,3-dimethylimidazolinium chloride (0.11 mL) were added in that order to a chloroform (0.30 mL) solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (30 mg), and stirred at room temperature for 1 hour. The reaction liquid was concentrated and purified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=from 10% to 95%, gradient) to give the entitled compound (26 mg, 65%) as a white crystal.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. custompurified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=from 10% to 95%, gradient)

Sources & evidence

ORD record
ord-d71fb545cf914fc5a1a711f2adb6ac1f
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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