1H-indol-4-ol → Benzyl 4-[4-(1H-indol-4-yloxymethyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1176649Notes

Reaction equation

HRID 1176649 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH:10]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]3[O:35][CH2:34][CH2:33][N:32]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:31]=3[CH:41]=2)=[CH:5][CH:4]=1.[OH:42][C:43]1[CH:51]=[CH:50][CH:49]=[C:48]2[C:44]=1[CH:45]=[CH:46][NH:47]2>>[NH:47]1[C:48]2[C:44](=[C:43]([O:42][CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH:9]4[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[O:16])[CH2:11][CH:10]4[O:25][CH2:26][C:27]4[CH:28]=[CH:29][C:30]5[O:35][CH2:34][CH2:33][N:32]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:31]=5[CH:41]=4)=[CH:5][CH:4]=3)[CH:51]=[CH:50][CH:49]=2)[CH:45]=[CH:46]1

Participants

3

Reactant 2

HCID 754211H-indol-4-olHCID 68501265HCID 68501265, compound

Product 1

HCID 68501215Benzyl 4-[4-(1H-indol-4-yloxymethyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Procedure

Analogously to Method I, 0.150 g of benzyl 4-(4-chloromethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 270b) and 0.0529 g of 4-hydroxyindole are reacted. The title compound is obtained as a violet oil. Rf=0.10 (1:2 EtOAc-heptane); Rt=5.58.

Sources & evidence

ORD record
ord-2486cff697304a98bc37f9ee896619cb
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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