Hydrochloric Acid → 4-Benzyl-6-(3,4-dichlorophenyl)-6-[2-[4-phenyl-4-(pyrrolidin-1-ylcarbonylamino)piperid-1-yl]ethyl]morpholin-3-one hydrochloride monohydrate

HRID 362732Notes

Reaction equation

HRID 362732 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)([CH2:14][CH2:15]OS(C)(=O)=O)[O:11][CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(O)(=O)=O)C=CC=CC=1.[C:40]1([C:46]2([NH:52][C:53]([N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:54])[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.CCOCC.O>[OH2:11].[ClH:27].[CH2:1]([N:8]1[CH2:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)([CH2:14][CH2:15][N:49]2[CH2:50][CH2:51][C:46]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([NH:52][C:53]([N:55]3[CH2:56][CH2:57][CH2:58][CH2:59]3)=[O:54])[CH2:47][CH2:48]2)[O:11][CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 195913894-Benzyl-6-(3,4-dichlorophenyl)-6-[2-(methanesulfonyloxy)ethyl]morpholin-3-oneHCID 212004754-Phenyl-4-(pyrrolidin-1-ylcarbonylamino)piperidine benzenesulfonate

Product 1

HCID 212005004-Benzyl-6-(3,4-dichlorophenyl)-6-[2-[4-phenyl-4-(pyrrolidin-1-ylcarbonylamino)piperid-1-yl]ethyl]morpholin-3-one hydrochloride monohydrateYield 65.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.1 g of the compound obtained in step B of EXAMPLE 14, 1.2 g of 4-phenyl-4-(pyrrolidin-1-ylcarbonylamino)piperidine benzenesulfonate and 0.95 g of K2CO3 in 3 ml of DMF is heated at 80°-100° C. for 3 hours. After cooling to RT, the reaction mixture is poured into water and the precipitate formed is wrung, washed with water and dried under vaccum. The precipitate is chromatographed on silica H using a DCM/MeOH mixture (from 100/2; v/v to 100/3; v/v) as the eluent. The product obtained is dissolved in the minimum amount of DCM and acidified to pH 1 by the addition of a saturated solution of gaseous HCl in ether and the precipitate formed is strung to give 0.54 g of the expected product. M.p.=158°-160° C.

Workup

  1. temperatureis heated at 80°-100° C. for 3 hours
  2. customthe precipitate formed
  3. washwashed with water
  4. customdried under vaccum
  5. customThe precipitate is chromatographed on silica H
  6. customThe product obtained
  7. customthe precipitate formed

Sources & evidence

ORD record
ord-a127ffdd212d448b95d28ea1ccde0b29
Source dataset
uspto-grants-1999_02
Patent number
US05869663

Reaction notes

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