Hydrochloric Acid → 4-Piperidineethanol, 1-benzoyl-

HRID 1599469Notes

Reaction equation

HRID 1599469 reaction equation
C([BH-](CC)CC)C.[Li+].[C:9]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][C:24](OCC)=[O:25])[CH2:19][CH2:18]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.Cl>O1CCCC1>[C:9]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]1)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 103336094-Piperidineacetic acid, 1-benzoyl-, ethyl esterHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 104214984-Piperidineethanol, 1-benzoyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium triethylborohydride (100 ml, 1M solution in tetrahydrofuran) was added dropwise to a solution of ethyl 1-benzoyl-4-piperidineacetate (13.8 g) in dry tetrahydrofuran (50 ml) at 0° C. under nitrogen over 20 minutes whilst maintaining the temperature at 0°-5° C. The mixture was stirred at 0° C. for a further hour, allowed to warm to 20° C. and then water (50 ml) was added slowly. The mixture was acidified with a slight excess of dilute hydrochloric acid and extracted with ethyl acetate. The combined ethyl acetate extracts were washed (dilute hydrochloric acid, brine), dried and evaporated to give 1-benzoyl-4-(2-hydroxyethyl)piperidine as an oil.

Workup

  1. temperaturewhilst maintaining the temperature at 0°-5° C
  2. temperatureto warm to 20° C.
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed (dilute hydrochloric acid, brine)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e91f7961f05e4377bd089595c7747dc2
Source dataset
uspto-grants-1998_04
Patent number
US05741800

Reaction notes

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