Dimethylamine → 4-(1-Naphthyl)-2,2-dimethyl-7-(3-dimethylamino-2-hydroxypropoxy)-2H chromene

HRID 2163364

Reaction equation

HRID 2163364 reaction equation
[O:1]1[CH2:27][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1.[CH3:28][NH:29][CH3:30]>C(O)C>[C:17]1([C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:27][N:29]([CH3:30])[CH3:28])=[CH:6][CH:7]=3)[O:12][C:11]([CH3:16])([CH3:15])[CH:10]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 233307422,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyran

Product 1

HCID 541793584-(1-Naphthyl)-2,2-dimethyl-7-(3-dimethylamino-2-hydroxypropoxy)-2H chromene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(2,3-Epoxypropoxy)-2,2-dimethyl-4-(1-naphthyl)-2H-chromene (4.4g., 0.012 moles) was dissolved in a solution of dimethylamine in ethanol (28ml., ~40% solution) and left to stand at room temperature for 48 hours. Removal of solvent gave the title product as an orange oil which was converted to the hydrochloride salt. Recrystallization from acetone gave a white solid (3.13g., 64%) m.p. 185-187° C.

Workup

  1. waitleft
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-df428abecd194218b9f4fda582eecb4f
Source dataset
uspto-grants-1979_01
Patent number
US04133883

Linked notes

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