Benzyl Alcohol → 4-Piperidin-1-yl-butyric acid benzyl ester

HRID 1604343Notes

Reaction equation

HRID 1604343 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH3:10].[CH3:16]CCCCC.N1CCCCC1.[CH3:28][CH:29]([OH:31])C>ClCCl.CCOCC.C(N(CC)CC)C.CCOCC>[CH2:1]([O:8][C:29](=[O:31])[CH2:28][CH2:10][CH2:9][N:11]1[CH2:14][CH2:15][CH2:16][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 244Benzyl Alcohol2×HCID 3776IsopropanolHCID 8058HexaneHCID 8082PiperidineHCID 8471Triethylamine

Product 1

HCID 543330064-Piperidin-1-yl-butyric acid benzyl ester

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 22234951Ether triethylamineSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromobutyrlchloride (6 g) was dissolved in dichloromethane (30 ml), and cooled to 0° C. under nitrogen. A solution containing benzyl alcohol (3.4 ml) and triethylamine (4.5 ml) in dichloromethane (35 ml) was added dropwise over 30 min. The mixture was stirred under nitrogen for 2 h. T.l.c. (10:1 hexane:ether) showed the complete disappearance of benzyl alcohol, and the formation of a less polar product. Piperidine (3.2 ml) was added and the resulting mixture heated under reflux for 18 h. The cooled mixture was partitioned between 2M hydrochloric acid (250 ml) and ether (250 ml). The aqueous layer was separated, basified with solid potassium carbonate until pH≥10, extracted with ether (2×250 ml), dried (MgSO4), and the solvent evaporated in vacuo to leave an orange oil. T.l.c. SiO2, ether:triethylamine (100:1), Rf=0.34 detection, u.v., IPA.

Workup

  1. additionwas added dropwise over 30 min
  2. temperaturethe resulting mixture heated
  3. temperatureunder reflux for 18 h
  4. customThe cooled mixture was partitioned between 2M hydrochloric acid (250 ml) and ether (250 ml)
  5. customThe aqueous layer was separated
  6. extractionextracted with ether (2×250 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated in vacuo
  9. customto leave an orange oil

Sources & evidence

ORD record
ord-e348ad1af77c4b3a93274728f5023f05
Source dataset
uspto-grants-1999_11
Patent number
US05994344

Reaction notes

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