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

HRID 2264786Notes

Reaction equation

HRID 2264786 reaction equation
[CH:1]([N:4]([CH:27]([CH3:29])[CH3:28])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:15]([O:24]C)[C:16](=C=O)[CH:17]=[C:18](OC)[CH:19]=1)[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].C1C[O:39][CH2:38]C1.[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]([CH2:38][OH:39])[CH:17]=[CH:16][C:15]=1[OH:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 68718528lithium aluminium hydride THFHCID 86594320HCID 86594320, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-N,N-diisopropyl-3-(2-methoxy-5-methoxy-carbonylphenyl)-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-dce095cf8841463886c431f2c173671f
Source dataset
uspto-grants-2010_12
Patent number
US07855230B2

Reaction notes

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