N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine → 2-(3-{[3-(2-BENZYLOXY-5-METHYLPHENYL)-3-PHENYLPROPYL]ISOPROPYLAMINO}-1-PHENYLPROPYL)-4-METHYLPHENOL

HRID 899564Notes

Reaction equation

HRID 899564 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[OH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].C([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][C:31]=1[C:37]1[C:38]([CH2:48][CH2:49][CH2:50][C:51]2C=CC=C[CH:52]=2)=C(S([O-])(=O)=O)C=C[C:42]=1[CH3:43])C1C=CC=CC=1>C(#N)C>[CH2:7]([O:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:43][CH2:42][CH:37]([C:31]1[CH:32]=[C:33]([CH3:36])[CH:34]=[CH:35][C:30]=1[OH:29])[C:38]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 9857017N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamineHCID 86604788HCID 86604788, compound

Product 1

HCID 115633772-(3-{[3-(2-BENZYLOXY-5-METHYLPHENYL)-3-PHENYLPROPYL]ISOPROPYLAMINO}-1-PHENYLPROPYL)-4-METHYLPHENOL

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
112.5 °C

Procedure

A mixture of N-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine (59 g) and 3-(2-(benzyloxy)-5-methylphenyl)-3-phenylpropyl-4-methylbenzenesulfonate of Formula IVa (100 g) in acetonitrile (595 ml) was heated in an autoclave at 110-115° C. for 16-18 hours. The reaction mass was cooled to 60-65° C., and solvent was distilled completely under vacuum. Charged ethyl acetate (290 ml) and water (590 ml) to the residue. Separated the aqueous layer and extracted with 118 ml of ethyl acetate. Combined organic layers were washed with water (590 ml) and distilled completely to obtain 108 g of syrup. This syrup was loaded onto a silica gel column and eluted with 5% ethyl acetate in chloroform. Distilled the solvent completely to get 38 g of the title compound as syrup.

Workup

  1. temperatureThe reaction mass was cooled to 60-65° C.
  2. distillationsolvent was distilled completely under vacuum
  3. customSeparated the aqueous layer
  4. extractionextracted with 118 ml of ethyl acetate
  5. washCombined organic layers were washed with water (590 ml)
  6. distillationdistilled completely

Sources & evidence

ORD record
ord-1bec8830371c4d3db6a0faba9acdf4bb
Source dataset
uspto-grants-2008_04
Patent number
US07355077B2

Reaction notes

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