2-Naphthaleneethanol → 4-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine

HRID 1730357Notes

Reaction equation

HRID 1730357 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12]O.[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Ni].C1(C)C(C)=CC=CC=1>[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 738772-NaphthaleneethanolHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 214306134-Benzamido-1-[2-(2-naphthyl)ethyl]piperidine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7237O-XyleneSolvent

Procedure

2-(2-Naphthyl)ethanol (3.44 g., 0.02 mole), 4-benzamidopiperidine (4.08 g.,0.02 mole) and Raney Nickel (W7 ca. 5 g.) were suspended in xylene (200 ml.) and the stirred mixture boiled under reflux for 16 hours. Liberated water was removed by means of a Dean and Stark apparatus. The mixture was filtered hot and evaporated to ca. 100 ml. The resulting yellow solution was stored until crystallisation was complete. The title compound was obtained as off-white needles (3.30 g.), m.p. 189°-191° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customLiberated water was removed by means of a Dean and Stark apparatus
  3. filtrationThe mixture was filtered hot
  4. customevaporated to ca. 100 ml
  5. customThe resulting yellow solution was stored until crystallisation

Sources & evidence

ORD record
ord-8386390efefd4ccfa3ce9ad29a939501
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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