Methylamine → HCID 19010891, compound

HRID 1741775Notes

Reaction equation

HRID 1741775 reaction equation
[Cl:1][CH2:2][N:3]1[CH2:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][C:4]1=[O:21].[CH3:22][NH2:23]>C1(C)C=CC=CC=1.C1COCC1>[ClH:1].[CH3:22][NH:23][CH2:2][N:3]1[CH2:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][C:4]1=[O:21]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 15224690HCID 15224690, compound

Product 1

HCID 19010891HCID 19010891, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(Chloromethyl)-5,5-diphenyl-2-piperidinone (27 g) was added portionwise during 20 min. to a solution of methylamine (120ml) in a mixture of toluene (100 ml) and THF (100 ml) at -30° C. with stirring and the mixture was allowed to warm to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water and the organic solvent layer was washed with water and brine. The aqueous layers were re-extracted with ethyl acetate and then chloroform. All the organic extracts were combined and concentrated to give the crude title product as a solid which was converted to the hydrochloride salt by dissolution in isopropanol:methanol(5:1) and then adding portionwise a solution of hydrogen chloride in isopropanol until the medium was acidic. The solution was cooled overnight at 0°-5° C. and the hydrochloride salt of the title product was filtered of as a solid, mp 169°-171° C.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic solvent layer was washed with water and brine
  3. extractionThe aqueous layers were re-extracted with ethyl acetate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72b345dea54441a9a6fb90587ce73303
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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