Cyclohexanone → HCID 13753412, compound

HRID 1248847Notes

Reaction equation

HRID 1248847 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:22]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Al]>CO>[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH:16]3[CH2:17][CH2:18][N:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5359268AluminumHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 13753412HCID 13753412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.50 gram (1.8 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine, 6.68 gram (68.1 millimoles) of cyclohexanone, 0.49 gram of finely cut bits of aluminum foil and 15 milliliters of methanol were mixed together. To the mixture, 0.01 gram (0.04 millimole) of mercuric chloride was added and the resulting mixture stirred at ambient temperature for 24 hours at which time a TLC analysis indicated complete consumption of the starting material and formation of a new product. The reaction mixture was filtered successively through celite and silica gel to remove aluminum and mercury salts and the filtrate concentrated in vacuo to obtain a yellow oil which crystallized on trituration with acetonitrile. Recrystallization from acetonitrile produced purified 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cyclohexylpiperidine product as long, straw-colored needles of melting point 162°-164° C. in a yield of 490 milligrams (75 percent). Elemental analyses were as follows:

Workup

  1. customconsumption of the starting material and formation of a new product
  2. filtrationThe reaction mixture was filtered successively through celite and silica gel
  3. customto remove aluminum and mercury salts
  4. concentrationthe filtrate concentrated in vacuo
  5. customto obtain a yellow oil which
  6. customcrystallized on trituration with acetonitrile
  7. customRecrystallization from acetonitrile
  8. customproduced
  9. custompurified 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cyclohexylpiperidine product as long, straw-colored needles of melting point 162°-164° C. in a yield of 490 milligrams (75 percent)

Sources & evidence

ORD record
ord-a799a6fc57894449980aa3f2ae92893c
Source dataset
uspto-grants-1986_12
Patent number
US04626542

Reaction notes

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