Hydrochloric Acid → HCID 20225285, compound

HRID 1249202Notes

Reaction equation

HRID 1249202 reaction equation
[CH3:1][NH:2][C:3]([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][CH3:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)=O.CO.[ClH:30].C(OCC)C>O1CCCC1>[ClH:25].[ClH:30].[CH3:1][NH:2][CH2:3][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([O:26][CH3:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:15])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 20225208HCID 20225208, compound

Product 1

HCID 20225285HCID 20225285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-[2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine (0.50 g; 85:15 mixture of diastereoisomers) in dry tetrahydrofuran (20 ml) was added borane-methyl sulphide complex (2 ml), under nitrogen. The solution was boiled under reflux for 3 hours, and after cooling to room temperature, methanol (6 ml) was added. This solution was allowed to stand overnight at room temperature, boiled under reflux for 1 hour, cooled, and hydrogen chloride gas passed through for 10 minutes. After dilution with diethyl ether, cooling to 0° C. and filtering, N-[2-(4-(2-methylaminoethoxy)phenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine dihydrochloride, mp 270°-273° C. (methanol-ethyl acetate), was obtained as a single diastereoisomer.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. custompassed through for 10 minutes
  5. filtrationfiltering

Sources & evidence

ORD record
ord-ec7ab5446eb548aba9e29df47c96cee6
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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