4-Benzylpiperidine → HCID 21709143, compound

HRID 324976Notes

Reaction equation

HRID 324976 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([CH2:13]Cl)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[C:1]1([C:7]2[N:12]=[C:11]([CH2:13][N:25]3[CH2:26][CH2:27][CH:22]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:23][CH2:24]3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 317384-BenzylpiperidineHCID 81531DiisopropylethylamineHCID 21709149HCID 21709149, compound

Product 1

HCID 21709143HCID 21709143, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 50 mg of 2-phenyl-4-chloromethylpyrimidine in 5 mL chloroform was added 80 mg 4-benzylpiperidine and 1 mL of N,N-diisopropylethylamine. The reaction mixture was heated at reflux temperature for 4 hr, cooled to room temperature, washed with 5 mL 1 N sodium hydroxide solution and the solvent removed by evaporation under reduced pressure to yield 2-phenyl-4-[(4-benzyl-piperidin-1-yl)rnethyl]-pyrimidine. This material was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluent. Evaporation of the solvent yielded a solid which was treated with ethereal-HCl to give 15 mg of 2-phenyl-4-[(4-benzyl-piperidin-1-yl)methyl]-pyrimidine dihydrochloride (Compound 11), mp 211-213° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 4 hr
  3. washwashed with 5 mL 1 N sodium hydroxide solution
  4. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8136c6922680479daf0cc3e5e2a9704b
Source dataset
uspto-grants-2001_04
Patent number
US06221871B1

Reaction notes

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