Methylamine → HCID 20186775, compound

HRID 2309008Notes

Reaction equation

HRID 2309008 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:26][CH2:27][CH2:28][OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].[CH3:30][NH2:31]>C(O)C>[ClH:25].[CH3:30][NH:31][C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:26][CH2:27][CH2:28][OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21285459HCID 21285459, compound

Product 1

HCID 20186775HCID 20186775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-hydroxyethoxy)-2-(3-chlorophenyl)ethanamine (4.0 g) and 33% methylamine in ethanol (50 ml) was heated under reflux for 1.5 h. The mixture was evaporated under reduced pressure and the residue converted to its hydrochloride by addition of ethereal hydrogen chloride. Recrystallisation from ethyl acetate-methanol gave the title compound, mp. 117°-121° C. as a 56:44 mixture of diastereoisomers.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. customThe mixture was evaporated under reduced pressure
  4. additionthe residue converted to its hydrochloride by addition of ethereal hydrogen chloride
  5. customRecrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-a3d7d059f30744e193bf503e17563581
Source dataset
uspto-grants-1987_09
Patent number
US04692465

Reaction notes

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