Ammonium Hydroxide → 4-[1,2,3,6-Tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine

HRID 1989875Notes

Reaction equation

HRID 1989875 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)(O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH4+:23].[OH-]>>[C:3]1([CH2:2][N:9]2[CH2:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([NH2:23])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 179894681-Benzyl-4-(p-bromophenyl)-4-piperidinol hydrochloride

Product 1

HCID 224994164-[1,2,3,6-Tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine

Conditions

Temperature
180 °C

Procedure

A mixture of 1-benzyl-4-(p-bromophenyl)-4-piperidinol hydrochloride (0.23 mol) and Cu2O (2 g) in NH4OH (500 ml) was stirred at 180° C. for 12 hours. The mixture was cooled, extracted with DCM and washed with water. The organic layer was dried, filtered off and evaporated, yielding 60 g of 4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine (intermediate 47).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with DCM
  3. washwashed with water
  4. customThe organic layer was dried
  5. filtrationfiltered off
  6. customevaporated

Sources & evidence

ORD record
ord-e8435a6da6864c6d8cfa026bdcdee4e2
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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