Methyl 3-piperidinocarbonylbenzoate → (3-((Piperidin-1-yl)methyl)phenyl)methanol

HRID 35602Notes

Reaction equation

HRID 35602 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18](OC)=[O:19])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[N:7]1([CH2:13][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[CH2:18][OH:19])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 17175211Methyl 3-piperidinocarbonylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7164645(3-((Piperidin-1-yl)methyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (5 g) was added portionwise to a stirred solution of methyl 3-piperidinocarbonylbenzoate (12.9 g) in dry tetrahydrofuran (200 ml) under nitrogen and the mixture was stirred under reflux for 3 hours. Excess reducing agent was destroyed by the dropwise addition of water under nitrogen with cooling. The reaction mixture was filtered through diatomaceous earth (sold under the trade name CELITE) which was washed with water and ethyl acetate and then the organic layer was separated. The aqueous layer was washed with ethyl acetate. The combined extracts were washed with water, dried and evaporated to give 3-piperidinomethylbenzylalcohol.

Workup

  1. temperatureunder reflux for 3 hours
  2. customwas destroyed by the dropwise addition of water under nitrogen
  3. temperaturewith cooling
  4. filtrationThe reaction mixture was filtered through diatomaceous earth (
  5. washwas washed with water and ethyl acetate
  6. customthe organic layer was separated
  7. washThe aqueous layer was washed with ethyl acetate
  8. washThe combined extracts were washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-244c2b01443c41be95d54f233756fa40
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

Loading…