Dimethylamine → 5-(3-Dimethylamino-2-hydroxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2413018Notes

Reaction equation

HRID 2413018 reaction equation
[O:1]1[CH2:20][CH:2]1[CH2:3][C:4]1([OH:19])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[CH3:21][NH:22][CH3:23]>CCO>[CH3:21][N:22]([CH3:23])[CH2:20][CH:2]([OH:1])[CH2:3][C:4]1([OH:19])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 204314525-(2,3-Epoxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 204314555-(3-Dimethylamino-2-hydroxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.7 g (14 mmol) of the epoxide 11, 26.8 g (0.59 mol) of anhydrous dimethylamine, and 50 ml of EtOH was heated at 100° C. in a stainless steel autoclave for 12 hrs. When cool the contents were removed and concentrated under reduced pressure. Recrystallization of the solid residue from aqueous EtOH afforded 1.6 g (37% yield) of the crystalline amino-diol 12, m.p. 144°-146° C.

Workup

  1. temperatureWhen cool the contents
  2. customwere removed
  3. concentrationconcentrated under reduced pressure
  4. customRecrystallization of the solid residue from aqueous EtOH

Sources & evidence

ORD record
ord-9e7f3d8b09e54cb2ac5c2c3d434de530
Source dataset
uspto-grants-1985_01
Patent number
US04495281

Reaction notes

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