1-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-one → 3-[3-(3-{3-[1-Methyl-3-oxo-3-(2,6,6-trimethyl-cyclohex-3-enyl)-propylamino]-propylamino}-propylamino)-propylamino)-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one

HRID 855492

Reaction equation

HRID 855492 reaction equation
[CH3:1][CH:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=[O:14])[CH:11]=[CH:12][CH3:13].[NH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][CH2:26][NH2:27]>C(O)C>[CH3:13][CH:12]([NH:27][CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][NH:15][CH:12]([CH3:13])[CH2:11][C:10]([CH:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH:6]=[CH:7][CH:2]1[CH3:1])=[O:14])[CH2:11][C:10](=[O:14])[CH:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH:6]=[CH:7][CH:2]1[CH3:1]

Participants

4

Reactant 2

HCID 422961-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-oneHCID 78350Norspermine

Product 1

HCID 235913683-[3-(3-{3-[1-Methyl-3-oxo-3-(2,6,6-trimethyl-cyclohex-3-enyl)-propylamino]-propylamino}-propylamino)-propylamino)-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. stirred solution of 96 g (0.50 mol) of 1-(2,6,6-trimethyl-cyclohex-3-enyl)-but-2-en-1-one (δ-damascone) in 250 mL of ethanol is added 47 g (0.25 mol) of N1-[3-(3-Amino-propylamino)-propyl]-propane-1,3-diamine. The reaction is allowed to warm to room temperature. After stirring for 24 h, the ethanol is concentrated by rotary evaporation to give 3-[3-(3-{3-[1-methyl-3-oxo-3-(2,6,6-trimethyl-cyclohex-3-enyl)-propylamino]-propylamino}-propylamino)-propylamino]-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one (bis-Michael adduct 14) as an oil.

Workup

  1. concentrationthe ethanol is concentrated by rotary evaporation

Sources & evidence

ORD record
ord-bf5b2c0f68204de6a5dd23ba53ef5b38
Source dataset
uspto-grants-2007_08
Patent number
US07262156B2

Linked notes

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