Dimethylamine → HCID 20223266, compound

HRID 437270Notes

Reaction equation

HRID 437270 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH:8]([CH3:12])[CH2:9][CH:10]=O)[CH2:4][CH:3]=1.[CH3:13][NH:14][CH3:15].[H][H]>[Pt]=O.C(O)C>[CH3:13][N:14]([CH3:15])[CH2:10][CH2:9][CH:8]([CH:5]1[CH2:6][CH2:7][C:2]([CH3:1])=[CH:3][CH2:4]1)[CH3:12]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 1109233-Cyclohexene-1-propanal, beta,4-dimethyl-HCID 178418361HCID 178418361, compound2×

Product 1

HCID 20223266HCID 20223266, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A 250 ml hydrogenation flask was charged with 50g (0.3 mole ) of 3-(4-methyl-3-cyclohexenyl)butyraldehyde, 15g (0.33 mole) of dimethylamine, 0.5 of platinum oxide and 80 ml of 95% ethanol. Cooling was required to control the initial exotherm. The reaction mixture was then shaken at ambient temperature under 20-40 lbs. of hydrogen until 0.3 mole of hydrogen was consumed. The mixture ws filtered and concentrated, and the residue was distilled yielding 38.4g of pure N,N-dimethyl-N-[3-(4-methyl-3-cyclohexenyl)butyl]amine: bp 95-101 (0.4mm); ir (τ max. film) 3.5 (s), 6.9 (s), 7.3 (s), 12.5 (m) micron; nmr (8 CDCl3), 5.40 (m, 1H), 2.28 (s, 8H), 2.0 to 0.8 (m, 16H) ppm; ms (molecular ion) 195.

Workup

  1. temperatureCooling
  2. filtrationThe mixture ws filtered
  3. concentrationconcentrated
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-97f0c835d2194daa8e7752eefbf20243
Source dataset
uspto-grants-1977_06
Patent number
US04030908

Reaction notes

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