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Aluminum(III) Chloride → 2-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

HRID 50596
Notes
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Reaction equation

HRID 50596 reaction equation
[CH:1]([N:4]([CH:27]([CH3:29])[CH3:28])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([C:20](OC)=[O:21])[CH:17]=[CH:16][C:15]=1[O:24]C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1>[CH:27]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][C:15]=1[OH:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 12972418(+/-)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamideHCID 68718528lithium aluminium hydride THF

Product 1

HCID 99279712-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of (±)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamide (0.79 g, 2.0 mmol) in 20 ml of tetrahydrofuran was cooled to 5° C. and then treated with 2.5 ml of 1M LiAlH4/THF. After stirring at room temperature for 18 hrs. finely powdered aluminium chloride (0.3 g) was added and stirring was continued for additional 4 hrs. The reaction was quenched at 5° C. by the dropwise addition of water followed by aqueous sodium hydroxide solution. The mixture was diluted with diethyl ether (150 ml) and the organic phase was washed with half saturated brine, dried (sodium sulphate), and evaporated to dryness to give the title compound as a solid off-white foam. Tlc (2) 0.16, m.p. 48-51° C. A portion of the material was converted into the hydrochloride (ethereal hydrochloric acid), m.p. 186-189° C. (dec.).

Workup

  1. stirringstirring
  2. waitwas continued for additional 4 hrs
  3. customThe reaction was quenched at 5° C. by the dropwise addition of water
  4. additionThe mixture was diluted with diethyl ether (150 ml)
  5. washthe organic phase was washed with half saturated brine
  6. dry with materialdried (sodium sulphate)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5f12306441c344ecbf57874da1e4b96e
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713464B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes