Potassium Carbonate → 1-(2-(2,3,4,5-Tetrahydro-7-cyano-1-benzoxepin-5-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

HRID 2396881Notes

Reaction equation

HRID 2396881 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][CH2:9][CH:8]([CH2:13][CH2:14]Br)[C:7]=2[CH:16]=1)#[N:2].[H-].C([Al+]CC(C)C)C(C)C.Cl.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].C([O-])([O-])=O.[K+].[K+]>CC(CC)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][CH2:9][CH:8]([CH2:13][CH2:14][N:41]3[CH2:40][CH2:39][CH:38]([C:32]4[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:30]([O:29][CH3:28])[CH:31]=4)[CH2:43][CH2:42]3)[C:7]=2[CH:16]=1)#[N:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 189865192-(2,3,4,5-Tetrahydro-7-cyano-1-benzoxepin-5-yl)ethyl bromideHCID 189865774-(3,4-Dimethoxyphenyl)piperidine hydrochlorideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 189865231-(2-(2,3,4,5-Tetrahydro-7-cyano-1-benzoxepin-5-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3.6 g of 2-(2,3,4,5-tetrahydro-7-cyano-1-benzoxepin-5-yl)ethyl bromide [obtainable starting from 2,3,4,5-tetrahydro-7-cyano-1-benzoexpin-5-one [sic] by reaction with triphenylethylphosphinium bromide, subsequent bromination of the product in the allyl position and reduction of the isolated double bond with diisobutyl-aluminiumhydride (DIBAH)], 1 equivalent of 4-(3,4-dimethoxyphenyl)piperidine hydrochloride, 3.8 g of K2CO3 and 2.1 g of KI are dissolved in 120 ml of ethyl methyl ketone and the mixture is boiled for 3 hours. Customary working up gives 1-(2-(2,3,4,5-tetrahydro-7-cyano-1-benzoxepin-5-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine.

Sources & evidence

ORD record
ord-af3eb4b01e1c4d9da7abb7616e6fe4d6
Source dataset
uspto-grants-1996_02
Patent number
US05495022

Reaction notes

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