Aniline → N-phenyl-5-(4-(3,4-dimethoxyphenyl)piperidino)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amine

HRID 1272328Notes

Reaction equation

HRID 1272328 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]4[O:31][C:30]([CH3:33])([CH3:32])[CH:29](O)[C:28]=4[C:35]=3[CH3:36])[CH2:20][CH2:19]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]>CO>[C:2]1([NH:1][CH:29]2[C:28]3[C:35]([CH3:36])=[C:24]([N:21]4[CH2:20][CH2:19][CH:18]([C:12]5[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([O:9][CH3:8])[CH:11]=5)[CH2:23][CH2:22]4)[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]=3[O:31][C:30]2([CH3:33])[CH3:32])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 674206985-(4-(3,4-Dimethoxyphenyl)piperidino)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol

Product 1

HCID 10207226N-phenyl-5-(4-(3,4-dimethoxyphenyl)piperidino)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amineYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using aniline and 5-(4-(3,4-dimethoxyphenyl)piperidino)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol obtained in Reference Example 19, the title compound was synthesized in the same manner as in Example 58. Yield 60%. mp. 138–140° C. (methanol).

Workup

  1. customobtained in Reference Example 19

Sources & evidence

ORD record
ord-7c2ef0523fcf40f1b9fc71510c712810
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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