1,1-Dimethoxyethyl(dimethyl)amine → HCID 20459997, compound

HRID 1156546Notes

Reaction equation

HRID 1156546 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].C[O:19][C:20](OC)([N:22]([CH3:24])[CH3:23])[CH3:21]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:21][C:20]([N:22]([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 4311764Sodium borohydrideHCID 114583403-(3-Methoxyphenyl)cyclohex-2-enone

Product 1

HCID 20459997HCID 20459997, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10 g of 3-(m-methoxyphenyl)-2-cyclohexen-1-ol obtained by reducing 3-(m-methoxyphenyl)-2-cyclohexene-1-one with sodium borohydride, are dissolved in 100 ml of xylene, whereupon 12 g of N,N-dimethylacetamide dimethyl acetal are added, and the mixture is boiled at reflux for 8 hours. After distillation of the solvent, the oil remaining behind is chromatographed on a 30-fold amount of silica gel. The fractions which are uniform in accordance with thin-layer chromatography and which are produced by elution with methylene chloride, are combined and evaporated, and there is obtained pure 1-(m-methoxyphenyl)-N,N-dimethyl-3-cyclohexene-1-acetamide in the form of a pale yellowish oil.

Workup

  1. additionare added
  2. temperatureat reflux for 8 hours
  3. distillationAfter distillation of the solvent
  4. customthe oil remaining behind is chromatographed on a 30-fold amount of silica gel
  5. customare produced by elution with methylene chloride
  6. customevaporated

Sources & evidence

ORD record
ord-4aee8ff11625442997e576c5bd4d8718
Source dataset
uspto-grants-1982_06
Patent number
US04336268

Reaction notes

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