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

HRID 852449Notes

Reaction equation

HRID 852449 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH3:22]>>[C:15]1([CH2:14][N:11]2[CH2:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:22])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 53335251-Benzyl-4-(4-bromophenyl)piperidin-4-ol

Product 1

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

Conditions

Temperature
180 °C

Procedure

A mixture of 4-(4-bromophenyl)-1-(phenylmethyl)-4-piperidinol (0.23 mole) and Cu2O (2 g) in aqueous ammonia (500 ml) was stirred at 180° C. for twelve 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.

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-86f332635f4b4f5b816183bb6857ab37
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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