Formaldehyde → HCID 54058166, compound

HRID 1580448Notes

Reaction equation

HRID 1580448 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH2:6])=[S:5].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:20]=O>CO>[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH:6][CH2:20][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[S:5]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 15581943α-(1-Methylethyl)-2-pyridineethanethioamide

Product 1

HCID 54058166HCID 54058166, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 1.0 g. (0.005 mole) of 3-methyl-2-(2-pyridyl)thiobutanamide in 20 ml. of methanol is treated with 0.65 g. (0.0075 mole) of piperidine and then with 0.23 g. of formaldehyde. The mixture is kept for 72 hours at 25°C., then concentrated in vacuo at 25°C. The residue is suspended in water and then extracted into chloroform. The chloroform is evaporated from the extracts and the residue is dissolved in hexane and cooled to -60°C. on a dry ice bath. Upon warming to 25°C., the hexane solution was decanted from insoluble oil and then evaporated in vacuo. The residue is vacuum dried at 0.005 mm. and 25°C. to give 3-methyl-N-piperidinomethyl-2-(2-pyridyl)thiobutanamide.

Workup

  1. concentrationconcentrated in vacuo at 25°C
  2. extractionextracted into chloroform
  3. customThe chloroform is evaporated from the extracts
  4. dissolutionthe residue is dissolved in hexane
  5. temperatureUpon warming to 25°C.
  6. customthe hexane solution was decanted from insoluble oil
  7. customevaporated in vacuo
  8. customdried at 0.005 mm

Sources & evidence

ORD record
ord-00d034655db049dd94098f2a15298f57
Source dataset
uspto-grants-1976_01
Patent number
US03932641

Reaction notes

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