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

HRID 1176641Notes

Reaction equation

HRID 1176641 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH:11]2[OH:26])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[CH2:28][C:29]1[CH:30]=[CH:31][C:32]2[O:37][CH2:36][C:35](=[O:38])[N:34]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:33]=2[CH:44]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:12][CH:11]2[O:26][CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][C:35](=[O:38])[N:34]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:33]=3[CH:44]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 468352236-(chloromethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 68500832Benzyl 4-(3-fluoro-4-methoxyphenyl)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 68499794Benzyl 4-(3-fluoro-4-methoxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Procedure

Analogously to Method D, 0.050 g of benzyl 4-(3-fluoro-4-methoxyphenyl)-3-hydroxypiperidine-1-carboxylate and 0.042 g of 6-chloromethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one are reacted. The title compound is obtained as a colourless resin. Rf=0.26 (2:1 EtOAc-heptane); Rt=5.10.

Sources & evidence

ORD record
ord-c6fae5aa54a9465f875f4c6393c36eb4
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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