Ethanol → 1-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]piperidine

HRID 596291Notes

Reaction equation

HRID 596291 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2.I[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]I.C(=O)([O-])[O-].[K+].[K+].C(O)C>O>[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:12][CH2:13][CH:14]([N:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:15][CH2:16]2

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 123541,5-DiiodopentaneHCID 122512743',4'-Dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride

Product 1

HCID 122512771-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The amine prepared from 1.5 g. of 3',4'-dihydrospiro[ cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride [I(c)] (prepared as in Example 10C), 1.9 g. of 1,5-diiodopentane and 1.6 g. of potassium carbonate in 18 ml. of ethanol is stirred at reflux temperature for about 18 hours. The mixture after cooling is diluted with water, the solid collected on a filter and recrystallized from methanol to give 1-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]piperidine [I(c)].

Workup

  1. temperatureat reflux temperature for about 18 hours
  2. temperatureThe mixture after cooling
  3. customthe solid collected on
  4. filtrationa filter
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7c153cc9bb6f44fd98660d54c38fcef6
Source dataset
uspto-grants-1977_03
Patent number
US04010201

Reaction notes

Loading…