Methyl vinyl ketone → HCID 10496762, compound

HRID 247098Notes

Reaction equation

HRID 247098 reaction equation
[O:1]=[C:2]([CH3:5])[CH:3]=[CH2:4].[CH3:6][NH:7][CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C>[CH3:6][N:7]([CH2:8][CH2:9][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:4][CH2:3][C:2](=[O:1])[CH3:5]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 119812N-Methyl-3,3-diphenylpropylamine

Product 1

HCID 10496762HCID 10496762, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.72 ml of 3-oxo-but-1-ene was added dropwise, over a period of 20 minutes and such that the temperature did not exceed 2°-3° C., to a cooled solution of 7.87 g of N-methyl-3,3-diphenylpropylamine in 7 ml of diethyl ether. The solution thus obtained was evaporated in vacuo at room temperature to give 10.3 g of N-methyl-N-(3,3-diphenylpropyl)-4-aminobutan-2-one (100%) as free base, shown to be practically pure by TLC (chloroform: methanol 9:1 by volume) which could be used as such for further reactions. This compound could be transformed into the corresponding hydrochloride (m.p. 133°-135° C.) by treating the free base with hydrogen chloride in diethyl ether, and crystallizing the product thus obtained first from acetone: ethyl acetate: isopropanol then from acetone.

Workup

  1. customThe solution thus obtained
  2. customwas evaporated in vacuo at room temperature

Sources & evidence

ORD record
ord-74121af37567471b9d76b1af7ebf1c7d
Source dataset
uspto-grants-1987_11
Patent number
US04705797

Reaction notes

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