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

HRID 437246

Reaction equation

HRID 437246 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-f0ae86a5d7d94fe7a08083e5cbbad43a
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Linked notes

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