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

HRID 366509

Reaction equation

HRID 366509 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-b4438eb1509d411faa60c37bf1570671
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Linked notes

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