Water → α,α-Bis(4-chlorophenyl)-4-piperidinemethanol

HRID 1709852Notes

Reaction equation

HRID 1709852 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)([OH:28])[CH:15]2[CH2:20][CH2:19][N:18](C(N(CC)CC)=O)[CH2:17][CH2:16]2)=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)([CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[OH:28])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14698740HCID 14698740, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14698743α,α-Bis(4-chlorophenyl)-4-piperidinemethanolYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 8.5 g (0.225 mole) of lithium aluminum hydride in 400 ml of anhydrous tetrahydrofuran was added a solution of 39.2 g (0.09 mole) of 4-[bis(4-chlorophenyl)hydroxymethyl]-N,N-diethyl-1-piperidinecarboxamide in 400 ml of tetrahydrofuran in a stream over a 15 min period. The mixture was heated at reflux for 24 hr, cooled, and treated successively with 8.5 ml of water, 25 ml of a 3N sodium hydroxide solution and 8.5 ml of water. The mixture was stirred for 0.5 hr and then filtered. The filtrate was concentrated under reduced pressure to give a gum which crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and recrystallized from benzene to yield 10.5 g (35%) of title compound as a white solid. An analytical sample was recrystallized from 2-propanol, mp 184°-188° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hr
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a gum which
  7. customcrystallized
  8. customThe solid was triturated with petroleum ether (30°-60° C.)
  9. filtrationcollected by filtration
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-e38d8574482f44a5ae2e23ef1b39c5d5
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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