Dimethylformamide → HCID 88805629, compound

HRID 1076968Notes

Reaction equation

HRID 1076968 reaction equation
[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:12](O)=[O:13])[CH2:8][CH2:7]1)#[N:2].CN(C)C=O.S(Cl)([Cl:40])=O>O1CCCC1>[ClH:40].[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:12]([Cl:40])=[O:13])[CH2:8][CH2:7]1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 34328Difenoxin

Product 1

HCID 88805629HCID 88805629, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 7 grams of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid suspended in 100 ml. of anhydrous tetrahydrofuran and 5 ml. of redistilled N,N-dimethylformamide is added 8 ml. of thionyl chloride in 50 ml. of anhydrous tetrahydrofuran. The resulting clear solution is stirred at room temperature under anhydrous conditions for about 5 minutes, then heated at the reflux temperature for 15 minutes and concentrated to dryness. To the residue is added an equal volume of tetrahydrofuran and the resultant mixture is contacted with a stream of nitrogen and stripped of solvent by vacuum distillation. The residue is triturated with cold tetrahydrofuran, then filtered. The filtrate is concentrated to dryness at room temperature in a nitrogen atmosphere. The solid residue is filtered with anhydrous ether and dried at room temperature in vacuo, thus affording 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid chloride hydrochloride, melting at about 169°-171°C. with decomposition. The product has the formula ##SPC10##

Workup

  1. temperatureheated at the reflux temperature for 15 minutes
  2. concentrationconcentrated to dryness
  3. additionTo the residue is added an equal volume of tetrahydrofuran
  4. distillationstripped of solvent by vacuum distillation
  5. customThe residue is triturated with cold tetrahydrofuran
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated to dryness at room temperature in a nitrogen atmosphere
  8. filtrationThe solid residue is filtered with anhydrous ether
  9. dry with materialdried at room temperature in vacuo, thus affording 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid chloride hydrochloride, melting at about 169°-171°C. with decomposition

Sources & evidence

ORD record
ord-2e2d1a4e33044bbb82c7ce33447bf460
Source dataset
uspto-grants-1976_05
Patent number
US03959275

Reaction notes

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