Hydrochloric Acid → HCID 54140316, compound

HRID 1458531Notes

Reaction equation

HRID 1458531 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].Cl[CH:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[OH-].[Na+].Cl>C(Cl)(Cl)Cl>[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH:12]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[OH:4])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1000PhenylethanolamineHCID 14798Sodium HydroxideHCID 16767631HCID 16767631, compound

Product 1

HCID 54140316HCID 54140316, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Amino-1-phenylethanol (2.50 g, 18.2 mmol) and 4-(3-chloro-3-phenylpropyl)morpholine (4.37 g, 18.2 mmol) were mixed and heated to cause reaction at 110° C. for 40 minutes. The resulting mixture was cooled to room temperature, and then dissolved into chloroform (200 ml). After the solution was chilled with ice, 1N NaOH was added so that the hydrochloride was libereated. The chloroform portion was collected and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (chloroform/methanol=100/1) to obtain 2.88 g of the titled compound as a yellow oil (Yield: 46.5%)

Workup

  1. temperatureheated
  2. customreaction at 110° C. for 40 minutes
  3. customThe chloroform portion was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe residue was purified by medium pressure silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-594c914995fe4381bdb3485f7e76f086
Source dataset
uspto-grants-1998_12
Patent number
US05852006

Reaction notes

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