Sodium Hydroxide → 4-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

HRID 1973801Notes

Reaction equation

HRID 1973801 reaction equation
[C:1]1([NH:7][C:8]2([C:22](OCC)=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1C=CC=CC=1>[C:1]1([NH:7][C:8]2([CH2:22][OH:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12298147Ethyl 1-phenethyl-4-(phenylamino)piperidine-4-carboxylate

Product 1

HCID 122982044-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred and gently refluxing solution of 43 parts of ethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate in 288 parts of dry benzene is added dropwise a solution of 33.9 parts of sodium dihydro-bis(2-methoxyethoxy)aluminate 70% in 72 parts of dry benzene without heating. Upon completion, stirring is continued for 3 hours at reflux. The reaction mixture is allowed to cool to room temperature overnight and poured onto 1000 parts of ice-water. The resulting emulsion is decomposed by the addition of a concentrated sodium hydroxide solution. The organic layer is separated and filtered over hyflo. The filter-cake is washed thoroughly with benzene. The filtrate is dried, filtered and evaporated. The residue is crystallized from 385 parts of 2,2'-oxybispropane. The crude solid product is filtered off and recrystallized from 2-propanol, yielding 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinemethanol; mp. 96.7° C.

Workup

  1. temperaturewithout heating
  2. stirringUpon completion, stirring
  3. temperatureat reflux
  4. customThe organic layer is separated
  5. filtrationfiltered over hyflo
  6. washThe filter-cake is washed thoroughly with benzene
  7. customThe filtrate is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from 385 parts of 2,2'-oxybispropane
  11. filtrationThe crude solid product is filtered off
  12. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-f84f901ee00a4d3b84d01a77cdfbc5f7
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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