Hydrochloric Acid → HCID 20225207, compound

HRID 1249201Notes

Reaction equation

HRID 1249201 reaction equation
Cl.[C:2]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:17][CH2:18][CH:19]([O:27][CH3:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH3:16])=[CH:10][CH:9]=1)(OC)=[O:3].[CH3:29][NH2:30].Cl>CO.[Cl-].[Na+]>[ClH:26].[CH3:29][NH:30][C:2]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:17][CH2:18][CH:19]([O:27][CH3:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH3:16])=[CH:10][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6329Methylamine3×HCID 20225212HCID 20225212, compound

Product 1

HCID 20225207HCID 20225207, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

To a solution of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine hydrochloride (0.63 g, diastereoisomeric ratio 92:8) in methanol was added 5 ml of a 30% aqueous solution of methylamine. This mixture was boiled under reflux for 6 hours during which time 3 further 5 ml portions of the methylamine solution were added. The solution was cooled to room temperature, a further 5 ml of methylamine solution added and the reaction mixture allowed to stand at room temperature overnight. After diluting with saturated sodium chloride solution the mixture was extracted with dichloromethane, washed with saturated sodium chloride solution, dried (magnesium sulphate), filtered and evaporated to give an oil which was converted to its hydrochloride salt by addition of ethereal hydrogen chloride. Recrystallisation from methanol-ethyl acetate gave the title compound, mp 217°-9° C., as single diastereoisomer.

Workup

  1. additionwere added
  2. extractionwas extracted with dichloromethane
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil which
  8. customRecrystallisation from methanol-ethyl acetate

Sources & evidence

ORD record
ord-3a2237a7705d44a1b2938630a7c5200b
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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