Pyridine → Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorohexanoate

HRID 280979Notes

Reaction equation

HRID 280979 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21](O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.N1C=CC=CC=1.S(Cl)([Cl:42])=O>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([Cl:42])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 13817553Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate

Product 1

HCID 19868892Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorohexanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate (12.8 g), ethyl acetate (120 ml) and pyridine (13 g) is added thionyl chloride (5.1 ml). The mixture is refluxed for 45 minutes with stirring. After cooling, the mixture is diluted with water (500 ml) and extracted with ethyl acetate (200 ml). The extract is washed successively with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue is chromatographed on silica gel using hexane-ethyl acetate (4:1) as an eluent to yield ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorohexanoate (10 g) as a colorless oil.

Workup

  1. temperatureThe mixture is refluxed for 45 minutes
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (200 ml)
  4. washThe extract is washed successively with 0.1N hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-621e5316b7a7425b96864655ff83aeb2
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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