Hydrochloric Acid → 3-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride

HRID 50060Notes

Reaction equation

HRID 50060 reaction equation
Cl.[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4].Cl.[C:21]([N:29]1[CH2:34][CH2:33][CH2:32][C:31]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=2)([CH2:35][CH2:36][CH2:37]N2CCC(C(N3CCCC3)=O)CC2)[CH2:30]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[ClH:57].[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:10][N:11]([CH2:37][CH2:36][CH2:35][C:31]2([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=3)[CH2:32][CH2:33][CH2:34][N:29]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:30]2)[CH2:12][CH2:13]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochlorideHCID 227417164-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride

Product 1

HCID 227417863-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochlorideYield 80.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.27 g of 4-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride, 0.45 g of the compound obtained in step B of EXAMPLE 1 and 0.3 g of K2CO3 in 3 ml of DMF is heated at 80° C. for 2 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.2 g of the expected product, m.p.=128° C.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with water and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent
  6. customThe product obtained
  7. customthe precipitate formed
  8. filtrationis filtered off

Sources & evidence

ORD record
ord-46ecda990008405c9949a5902ceea459
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Reaction notes

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