6-(chloromethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one → benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1176550Notes

Reaction equation

HRID 1176550 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:3]1.Cl[CH2:29][C:30]1[CH:31]=[CH:32][C:33]2[O:38][CH2:37][C:36](=[O:39])[N:35]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:34]=2[CH:45]=1>>[CH3:17][O:16][C:14]([C:11]1[CH:10]=[CH:9][C:8]([CH:7]2[CH2:6][CH2:5][N:4]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:3][CH:2]2[O:1][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][C:36](=[O:39])[N:35]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:34]=3[CH:45]=2)=[CH:13][CH:12]=1)=[O:15]

Participants

3

Reactant 2

HCID 468352236-(chloromethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 68497478HCID 68497478, compound

Product 1

HCID 68500724benzyl 4-(4-methoxycarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Procedure

Analogously to Method D, 5.25 g of benzyl 3-hydroxy-4-(4-methoxycarbonylphenyl)piperidine-1-carboxylate and 0.572 g of 6-chloromethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one are reacted. The title compound is obtained as a yellowish oil. Rf=0.28 (2:1 EtOAc-heptane). Rt=5.06.

Sources & evidence

ORD record
ord-4d924b6d54564d9aa298875ceae8dd32
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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