3-(Dimethylamino)propyl chloride hydrochloride → 4-(3'-Dimethylaminopropoxy)-3-phenyl-coumarin

HRID 904291Notes

Reaction equation

HRID 904291 reaction equation
[C:1]1([C:7]2[C:8](=[O:18])[O:9][C:10]3[C:15]([C:16]=2[OH:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24]Cl>>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][O:17][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8](=[O:18])[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 54688870Coumarin, 4-hydroxy-3-phenyl-

Product 1

HCID 233340314-(3'-Dimethylaminopropoxy)-3-phenyl-coumarinYield 59%

Procedure

By treating 10 g. (0.042 mol) of 3-phenyl-4-hydroxy-coumarin with 87 g. (0.055 mol) of 3-dimethylamino-1-chloropropane hydrochloride as described in Example 1, there are obtained 8.1 g. of a yellow oil which cannot be crystallised. Yield 59% (theoretical yield 13.6 g.).

Workup

  1. additionBy treating 10 g
  2. customare obtained 8.1 g
  3. customof a yellow oil which cannot be crystallised

Sources & evidence

ORD record
ord-21f0102d5124460a958c16ccd79fcf08
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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