Dichloromethane → HCID 53645814, compound

HRID 845430Notes

Reaction equation

HRID 845430 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(N(CC)CC)C.C(Cl)Cl.[C:32](Cl)(=[O:41])[CH:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C1C=CN=CC=1.CCOCC>[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]([C:32](=[O:41])[CH:33]=[CH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Product 1

HCID 53645814HCID 53645814, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

1.42 grams (5.15 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine, 1.56 grams (15.45 millimoles0 of triethylamine, 0.06 gram (0.51 millimoles) of 4-dimethylaminopyridine and 25 milliliters of methylene chloride were stirred together for 5 minutes and to the stirred solution, 0.86 gram (5.15 millimole) of cinnamoyl chloride was added in one portion. The resulting mixture was stirred for 0.5 hour at room temperature, then diluted with 200 milliliters of ether and the ethereal solution washed successively with two 200 milliliter portions of 2N hydrochloric acid, one 200 milliliter portion of sodium bicarbonate solution and one 300 milliliter portion of brine. The washed solution was dried over magnesium sulfate, and the solvent vaporized in vacuo from the dried solution to obtain as residue 1.6 grams of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cinnamoylpiperidine.

Workup

  1. additionwas added in one portion
  2. washthe ethereal solution washed successively with two 200 milliliter portions of 2N hydrochloric acid, one 200 milliliter portion of sodium bicarbonate solution and one 300 milliliter portion of brine
  3. dry with materialThe washed solution was dried over magnesium sulfate

Sources & evidence

ORD record
ord-47d3e78f2da4478aa380a531bed36010
Source dataset
uspto-grants-1988_07
Patent number
US04758577

Reaction notes

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