Water → 1-(3-Butynyl)-4-(4-chlorophenyl)piperidine

HRID 1279363Notes

Reaction equation

HRID 1279363 reaction equation
[C:1]([O-])(O)=O.[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]2CCNCC2)=[CH:9][CH:8]=1.[C:20]([C:24]1C=C(C=CC=1C)S([O-])(=O)=O)#[C:21]CC.O.[CH3:36][N:37]([CH3:40])[CH:38]=O>>[CH2:36]([N:37]1[CH2:40][CH2:14][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=2)[CH2:1][CH2:38]1)[CH2:24][C:20]#[CH:21]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 516892Sodium BicarbonateHCID 37327804-(4-Chlorobenzyl)piperidineHCID 184280043-Butynyltosylate

Product 1

HCID 184279681-(3-Butynyl)-4-(4-chlorophenyl)piperidine

Conditions

Temperature
0 °C

Procedure

A suspension of NaHCO3(4 g) and 4-[(4-chlorophenyl)methyl]piperidine (18 mmol) in dimethylformamide (DMF) (25 mL) is stirred under a N2 atm at 0° C., and treated dropwise with 3-butynyltosylate (20 mmol) as a solution in DMF (50 mL). The reaction mixture is heated at 80° C. and stirred an additional 18 hours. After cooling the reaction mixture is stirred vigorously with the addition of water (200 mL), and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The residue is purified by silica gel column chromatography (100:1 CH2Cl2:MeOH) to give 1-(3-butynyl)-4-(4-chlorophenyl)piperidine.

Workup

  1. temperatureThe reaction mixture is heated at 80° C.
  2. stirringstirred an additional 18 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by silica gel column chromatography (100:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-55c4a930c8b8476698b4f36da2dadb3c
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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