Hydrochloric Acid → 1-(4-Hydroxyphenyl)-2-[[2-[4-(phenylmethoxy)phenyl]ethyl](phenylmethyl)amino]-1-propanone

HRID 1404693Notes

Reaction equation

HRID 1404693 reaction equation
CS([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:39])[CH:13]([N:15]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[CH3:14])=[CH:8][CH:7]=1)(=O)=O.O.[OH-].[K+].Cl>CC(C)=O>[CH2:32]([N:15]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][CH:23]=1)[CH:13]([CH3:14])[C:12]([C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1)=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 56926830HCID 56926830, compound

Product 1

HCID 545759581-(4-Hydroxyphenyl)-2-[[2-[4-(phenylmethoxy)phenyl]ethyl](phenylmethyl)amino]-1-propanoneYield 96.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
59 °C

Procedure

50 g of 4-(2-{benzyl-[2-(4-benzyloxyphenyl)-ethyl]-amino}-propionyl)phenyl methanesulfonate (B), 100 ml of water, 355 ml of acetone and 18.4 g of potassium hydroxide are introduced into a one liter glass reactor at room temperature. The mixture is heated to reflux temperature (about 59° C.) and kept at such a temperature for two hours. Subsequently, the mixture is cooled down to 45-50° C. and 30% hydrochloric acid is added until a pH of around 7 is obtained. The lower phase is separated and the organic phase is diluted with 100 ml of water. A suspension is obtained that is cooled down to 0° C. The solid is isolated through filtration and washed and then vacuum dried at 40° C. 41.4 g of 2-{Benzyl-[2-(4-benzyloxy-phenyl)-ethyl]-amino}-1-(4-hydroxy-phenyl)-propan-1-one (C) as a white solid, are obtained.

Workup

  1. temperatureThe mixture is heated
  2. customfor two hours
  3. temperatureSubsequently, the mixture is cooled down to 45-50° C.
  4. customis obtained
  5. customThe lower phase is separated
  6. additionthe organic phase is diluted with 100 ml of water
  7. customA suspension is obtained
  8. temperaturethat is cooled down to 0° C
  9. customThe solid is isolated through filtration
  10. washwashed
  11. customvacuum dried at 40° C

Sources & evidence

ORD record
ord-d9a4a59cf23e4d8ca4d0f956624ae7d0
Source dataset
uspto-grants-2014_12
Patent number
US08912360B2

Reaction notes

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