Triethylamine → 1-[1-(4-Trifluoromethylphenylsulphonyl)-(4-piperidinylmethyl)]-4-(4-pyridyl)piperidine

HRID 1936569Notes

Reaction equation

HRID 1936569 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH2:18][CH2:17]1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][N:23]3[CH2:24][CH2:25][CH:26]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[CH2:27][CH2:28]3)[CH2:18][CH2:17]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 224622451-(4-Piperidinylmethyl)4-(4-pyridyl)piperidine hydrochloride

Product 1

HCID 699452071-[1-(4-Trifluoromethylphenylsulphonyl)-(4-piperidinylmethyl)]-4-(4-pyridyl)piperidineYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-trifluoromethylphenylsulphonyl chloride (394 mg) in methylene chloride (4 ml) was added dropwise over 15 minutes to a mixture of 1-(4-piperidinylmethyl)-4-(4-pyridyl)piperidine hydrochloride (550 mg) and triethylamine (1.07 ml) in dichloromethane (10 ml) at 0° C. The solution was stirred at ambient temperature for 18 hours. The solution was diluted with dichloromethane and washed with water, dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 2% methanol in dichloromethane. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-[1-(4-trifluoromethylphenylsulphonyl)-(4-piperidinylmethyl)]-4-(4-pyridyl)piperidine (395 mg): NMR (CDCl3): 1.30 (m, 2H), 1.45 (m, 1H), 1.80 (m, 6H), 2.00 (dt, 2H), 2.20 (d, 2H), 2.30 (dt, 2H), 2.40 (m, 1H), 2.90 (d, 2H), 3.80 (d, 2H), 7.10 (d, 2H), 7.80 (d, 2H), 8.50 (d, 2H); m/z 468 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by chromatography
  5. washeluting with 2% methanol in dichloromethane
  6. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2f6b147603c34419b0ef4c0c46137dee
Source dataset
uspto-grants-2002_05
Patent number
US06391880B1

Reaction notes

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