Acetone → HCID 13753411, compound

HRID 1248846Notes

Reaction equation

HRID 1248846 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.[CH3:22][C:23]([CH3:25])=O.[Al].N>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:23]([CH3:25])[CH3:22])[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 222AmmoniaHCID 5359268AluminumHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 13753411HCID 13753411, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.50 gram (1.8 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine (prepared in a manner described in the preceding example), 3.96 grams (68.1 millimoles) of acetone and 5 milliliters of methanol were warmed gently to start dissolution. To this was added 0.30 gram (11 millimoles) of aluminum bits and a catalytic amount (0.01 gram; 0.04 millimole) of mercuric chloride and the resulting mixture stirred for 2.5 hours. A TLC analysis of the reaction mixture showed presence of some but minor amount of product. The mixture was stirred for 48 hours. A TLC analysis at this time (1 percent methanol/99 percent chloroform saturated with ammonia) indicated consumption of the starting material with the formation of a new product which was determined by 1H NMR to be a 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-isopropylpiperidine product. The reaction mixture was filtered through a pad of celite and the solvent removed in vacuo to obtain a residue which after recrystallization from a minimum amount of hot acetonitrile and drying for 3.5 hours at 100° C./1 mm. Hg, was a white powder, m.p. 124°-126° C. The product had elemental analyses as follows:

Workup

  1. temperaturewere warmed gently
  2. dissolutiondissolution
  3. customconsumption of the starting material with the formation of a new product which
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. customthe solvent removed in vacuo
  6. customto obtain a residue which
  7. customafter recrystallization from a minimum amount of hot acetonitrile
  8. customdrying for 3.5 hours at 100° C./1 mm. Hg

Sources & evidence

ORD record
ord-177e2a6d12c241cd9ebad226c0a55fe9
Source dataset
uspto-grants-1986_12
Patent number
US04626542

Reaction notes

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