Hydrochloric Acid → 3-[Di(propan-2-yl)amino]-1-phenylpropan-1-ol

HRID 217308Notes

Reaction equation

HRID 217308 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:10]([NH:13][CH:14]([CH3:16])[CH3:15])([CH3:12])[CH3:11].[CH2:17]=O.Cl>CO.O>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][CH2:17][N:13]([CH:14]([CH3:16])[CH3:15])[CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7410AcetophenoneHCID 7912Diisopropylamine

Product 1

HCID 231376583-[Di(propan-2-yl)amino]-1-phenylpropan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

20.0 g of acetophenone is reacted with 18.7 g of diisopropylamine and 40 ml of water solution of formaldehyde in presence of 20 ml of conc. HCl in 360 ml of methanol for 2 hours at reflux temperature. After evaporation of most of methanol water and ethylacetate is added. After separation the organic phase was concentrated by evaporation and diluted with methanol. The dissolved compound is reduced with 4.2 g of sodium borohydride to yield 3-hydroxy-N,N-diisopropyl-3-phenylpropan-1-amine which may be converted into N,N-diisopropyl-3-phenylpropyl-2-ene-1-amine by treating with strong alkali.

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation of most of methanol water and ethylacetate
  3. additionis added
  4. customAfter separation the organic phase
  5. concentrationwas concentrated by evaporation
  6. additiondiluted with methanol

Sources & evidence

ORD record
ord-0f2c58701285495ba03eafb46d3b9c76
Source dataset
uspto-grants-2012_06
Patent number
US08193391B2

Reaction notes

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