N,N-Dimethylthioformamide → 4-(Diphenylmethyl)-1-piperidinecarbothioaldehyde

HRID 1413949Notes

Reaction equation

HRID 1413949 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:22]=[S:23]>C1(C)C=CC=CC=1>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH:22]=[S:23])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 69794N,N-DimethylthioformamideHCID 882784-Benzhydrylpiperidine

Product 1

HCID 130978784-(Diphenylmethyl)-1-piperidinecarbothioaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20.0 g (0.08 mole) of 4-diphenylmethylpiperidine, 14.2 g (0.16 mole) of N,N-dimethylthioformamide and 50 ml of toluene was refluxed for 12 hours, cooled, and washed with water. The organic layer was separated, dried and stripped to an oil which was treated with diethyl ether to give a solid. Recrystallization of this material afforded a white crystalline solid, 4-(diphenylmethyl)-1-piperidinecarbothioaldehyde, m.p. 152°-154° C.

Workup

  1. temperaturecooled
  2. washwashed with water
  3. customThe organic layer was separated
  4. customdried
  5. additionwas treated with diethyl ether
  6. customto give a solid
  7. customRecrystallization of this material

Sources & evidence

ORD record
ord-b44088f2149a48bdb88cede096132365
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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