4-(2-hydroxyphenyl)-N-methylbutyramide → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-{2-(3-methylcarbamoylpropyl)phenoxy]ethoxy}piperidine-1-carboxylate

HRID 1176397Notes

Reaction equation

HRID 1176397 reaction equation
[CH3:1][O:2][C:3]1[CH:47]=[CH:46][CH:45]=[CH:44][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1.[OH:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:55][CH2:56][CH2:57][C:58]([NH:60][CH3:61])=[O:59]>>[CH3:1][O:2][C:3]1[CH:47]=[CH:46][CH:45]=[CH:44][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32][O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH2:55][CH2:56][CH2:57][C:58](=[O:59])[NH:60][CH3:61])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 685011294-(2-hydroxyphenyl)-N-methylbutyramideHCID 86609984Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate

Product 1

HCID 68635256tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-{2-(3-methylcarbamoylpropyl)phenoxy]ethoxy}piperidine-1-carboxylate

Procedure

Analogously to Method G, 0.40 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate (Example 14b) and 0.23 g of 4-(2-hydroxyphenyl)-N-methylbutyramide are reacted. The title compound is obtained as a colourless resin. Rf=0.25 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.73.

Sources & evidence

ORD record
ord-3e1e9e19ecdb41cb9ffa3cb292e32250
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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