Ethanol → HCID 14253320, compound

HRID 845429Notes

Reaction equation

HRID 845429 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][N:23]([CH3:32])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C([BH3-])#N.[Na+].C(O)C>C(OCC)(=O)C>[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]([CH2:28][C:27]4[CH:30]=[CH:31][C:24]([N:23]([CH3:32])[CH3:22])=[CH:25][CH:26]=4)[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 74794-(Dimethylamino)BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 14253320HCID 14253320, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.00 gram (3.47 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine, 0.52 gram (3.47 millimoles) of p-dimethylaminobenzaldehyde, 0.63 gram (10.0 millimoles) of sodium cyanoborohydride and 10 milliliters of ethanol were stirred together at room temperature for 24 hours. At the end of this period, the mixture was diluted with 150 milliliters of ethyl acetate and the ethyl acetate solution washed successively with two 50 milliliter portions of 15 percent aqueous sodium bisulfite, one 50 milliliter portion of saturated sodium bicarbonate, and one 100 milliliter portion of brine and then dried over magnesium sulfate. The solvent was vaporized from the dried solution in vacuo to obtain a yellow oil. The oil was flash chromatographed on silica gel with 50/50 ethyl acetate/hexane as eluant to obtain 250 milligrams of a colorless oil which crystallized on standing overnight. The product after recrystallization from acetonitrile had a melting point of 163°-165° C. Elemental analyses of the product were as follows:

Workup

  1. washthe ethyl acetate solution washed successively with two 50 milliliter portions of 15 percent aqueous sodium bisulfite, one 50 milliliter portion of saturated sodium bicarbonate, and one 100 milliliter portion of brine
  2. dry with materialdried over magnesium sulfate
  3. customto obtain a yellow oil
  4. customchromatographed on silica gel with 50/50 ethyl acetate/hexane as eluant

Sources & evidence

ORD record
ord-f1edbe58273540819f1c3bf4323f6b2a
Source dataset
uspto-grants-1988_07
Patent number
US04758577

Reaction notes

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