Methylamine → 1-[(2,2-Dimethyl-4-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3-(methylamino)propan-2-ol

HRID 224923Notes

Reaction equation

HRID 224923 reaction equation
[O:1]1[CH2:23][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1.[CH3:24][NH2:25]>>[OH:1][CH:2]([CH2:23][NH:25][CH3:24])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 233307567-(2,3-Epoxypropoxy)-2,2-dimethyl-4-phenylchroman

Product 1

HCID 30464321-[(2,2-Dimethyl-4-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3-(methylamino)propan-2-ol

Procedure

Reaction of 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-phenylchroman with methylamine by an analogous method to that described in Example 2 gave 7-(2-hydroxy-3-methylaminopropoxy)-2,2-dimethyl-4-phenylchroman isolated as its hydrochloride salt, (57%), m.p. 182°-183°.

Sources & evidence

ORD record
ord-4925cdc074ee4674a32b53a0383df475
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Reaction notes

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