Dimethylamine → 7-(2-Hydroxy-3-dimethylaminopropoxy)-2,2-dimethyl-4-phenylchroman

HRID 838896Notes

Reaction equation

HRID 838896 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][NH:25][CH3:26]>C(O)C>[OH:1][CH:2]([CH2:23][N:25]([CH3:26])[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

4

Reactant 2

HCID 674DimethylamineHCID 233307567-(2,3-Epoxypropoxy)-2,2-dimethyl-4-phenylchroman

Product 1

HCID 30464287-(2-Hydroxy-3-dimethylaminopropoxy)-2,2-dimethyl-4-phenylchromanYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-phenylchroman (6.1g), anhydrous dimethylamine (15ml) and ethanol were left to stand at ambient temperature until tlc showed that reaction was complete (c. 2hrs.). Removal of the solvent in vacuo gave 7-(2-hydroxy-3-dimethylaminopropoxy)-2,2-dimethyl-4-phenylchroman (6.8g, 97%) isolated as the hydrochloride salt, m.p. 210°-215°, from acetone-ethanol.

Workup

  1. waitwere left
  2. customto stand at ambient temperature until tlc
  3. customshowed that reaction
  4. custom(c. 2hrs.)
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-409f720e4a6a4a0d881dbd751a452c02
Source dataset
uspto-grants-1978_06
Patent number
US04093631

Reaction notes

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