Hydrochloric Acid → 8-{2-[1,1-dimethyl-2-(4-hydroxyphenyl)ethylamino]-1-hydroxyethyl}-6-benzyloxy-4H-benzo[1,4]oxazin-3-one

HRID 12090Notes

Reaction equation

HRID 12090 reaction equation
O.[CH:2]([CH:4]=O)=[O:3].[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:25][C:26]([NH2:36])([CH3:35])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.Cl>>[CH3:35][C:26]([NH:36][CH2:4][CH:2]([C:16]1[C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=[C:14]([O:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:15]=1)[OH:3])([CH3:25])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 841394-HydroxyphentermineHCID 86593722(6-benzyloxy-4H-benzo[1,4]oxazin-3-one)-glyoxal hydrate

Product 1

HCID 220634878-{2-[1,1-dimethyl-2-(4-hydroxyphenyl)ethylamino]-1-hydroxyethyl}-6-benzyloxy-4H-benzo[1,4]oxazin-3-one

Procedure

The title compound is prepared from 10 g of (6-benzyloxy-4H-benzo[1,4]oxazin-3-one)-glyoxal hydrate and 4.6 g of 1,1-dimethyl-2-(4-hydroxyphenyl)ethylamine analogously to the method for Example 3(a). Yield: 9.0 g (64%, hydrochloride); melting point: 255° C.-258° C.

Sources & evidence

ORD record
ord-6d605ae120b142b89b2218dc15bdf324
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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