Allyl bromide → N,N-diethyl-4-[(3-methoxyphenyl)-(10-prop-2-enyl-9,10-diazatricyclo[4.2.1.12,5]decan-9-yl)methyl]benzamide

HRID 1912349Notes

Reaction equation

HRID 1912349 reaction equation
[CH:1]12[N:9]([CH:10]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[C:11]3[CH:23]=[CH:22][C:14]([C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH:6]([CH2:7][CH2:8]1)[CH:5]1[NH:32][CH:2]2[CH2:3][CH2:4]1.[CH2:33](Br)[CH:34]=[CH2:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:35]([N:32]1[CH:2]2[CH:1]3[N:9]([CH:10]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)[C:11]4[CH:23]=[CH:22][C:14]([C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=4)[CH:6]([CH:5]1[CH2:4][CH2:3]2)[CH2:7][CH2:8]3)[CH:34]=[CH2:33]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 672375014-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide

Product 1

HCID 53258062N,N-diethyl-4-[(3-methoxyphenyl)-(10-prop-2-enyl-9,10-diazatricyclo[4.2.1.12,5]decan-9-yl)methyl]benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture formed of the compound obtained in example 5.1 (0.98 mmoles), of allyl bromide (1.5 equivalents) and of anhydrous potassium carbonate (3 equivalents) in acetone (25 ml) is heated at reflux for 14 hours. At the end it is filtered and the filtrate is evaporated under vacuum. The compound 4-[(10-allyl-9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethyl benzamide (light solid) is obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 14 hours
  3. filtrationAt the end it is filtered
  4. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-db60b76b1b5d4a69a73f33faddbae21d
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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