Piperidine → 9-gamma-Piperidinopropyl-9,10-dihydro-9,10-methanoanthracene

HRID 27952Notes

Reaction equation

HRID 27952 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]12[CH2:19][CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=31)[C:11]1[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=1.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(OCC)(=O)C>[N:20]1([CH2:2][CH2:3][CH2:4][C:5]23[CH2:19][CH:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=42)[C:11]2[C:6]3=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 205199629-gamma-Chloropropyl-9,10-dihydro-9,10-methanoanthracene

Product 1

HCID 130690779-gamma-Piperidinopropyl-9,10-dihydro-9,10-methanoanthracene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-γ-chloropropyl-9,10-dihydro-9,10-methanoanthracene (50 mg) and piperidine (0.1 ml) was heated at 100° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-γ-piperidinopropyl-9,10-dihydro-9,10-methanoanthracene, which was converted into its hydrochloride. M.P. 280°-283° C.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-00217097ac874e0dbafe0515d61266bf
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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