Trifluoroacetic acid → 1-(Piperidin-4-ylcarbonyl)-4-(6-chloronaphthalen-2-yl-sulfonyl)piperazine Trifluoroacetate

HRID 431527Notes

Reaction equation

HRID 431527 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=4)[CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C1(OC)C=CC=CC=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>ClCCl>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:17][CH2:18][N:19]([S:22]([C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=4)[CH:26]=3)(=[O:24])=[O:23])[CH2:20][CH2:21]2)=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 121120201-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine

Product 1

HCID 187613891-(Piperidin-4-ylcarbonyl)-4-(6-chloronaphthalen-2-yl-sulfonyl)piperazine TrifluoroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-(1-Boc-piperidin-4-yl-carbonyl)-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine (2.2 g, 4.2 mmol) in dichloromethane (25 mL) was added anisole (2 mL) followed by TFA (25 mL). After 90 min, the solvents were removed in vacuo and the residue was dissolved in a few mL of dichloromethane and diluted with diethyl ether (200 mL). After stirring for 2 h, the suspension was sonicated and filtered and then the solid was washed with diethyl ether and dried in vacuo to give 2.25 g (99%) of a white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in a few mL of dichloromethane
  3. additiondiluted with diethyl ether (200 mL)
  4. customthe suspension was sonicated
  5. filtrationfiltered
  6. washthe solid was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-51990b05add0475a87b588a561d53a00
Source dataset
uspto-grants-2003_12
Patent number
US06660739B1

Reaction notes

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