Methylamine → HCID 67813946, compound

HRID 2172540Notes

Reaction equation

HRID 2172540 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]=[C:10]([CH2:21][CH2:22][CH2:23]O)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:31][NH2:32]>ClCCl.CN(C1C=CN=CC=1)C.C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]=[C:10]2[CH2:21][CH2:22][CH2:23][N:32]([CH3:31])[C:11]2=[N:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 6329MethylamineHCID 24819Phosphorus pentachlorideHCID 86702350HCID 86702350, compound

Product 1

HCID 67813946HCID 67813946, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

687 mg (1.99 mmol) of 2-{[(4-fluorophenyl)sulphanyl]methylene}-5-hydroxy-N-(4-methylphenyl)-pentanamide (prepared by the method described in WO 2010/070910) are dissolved in 25 ml of dichloromethane, and 828 mg (3.98 mmol) of phosphorus pentachloride are added. After 12 h of stirring at room temperature, all volatile components are removed under reduced pressure and the residue is suspended in 9 ml of triethylamine. 36.4 mg (0.297 mmol) of DMAP and 4.97 ml of 2M methanamine in THF are added to the reaction mixture. The mixture is stirred in a CEM microwave at 80° C. for 60 min (divided into three microwave vessels). The reaction mixture is diluted with water and extracted with ethyl acetate, and the organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 7.6 mg of N-(3-{[(4-fluorophenyl)sulphanyl]methylene}-1-methylpiperidin-2-ylidene)-4-methylaniline.

Workup

  1. customall volatile components are removed under reduced pressure
  2. stirringThe mixture is stirred in a CEM microwave at 80° C. for 60 min (divided into three microwave vessels)
  3. extractionextracted with ethyl acetate
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-e342491736994c73a8f8f734daeea658
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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