Hydrochloric Acid → 1-Benzoyl-3-[3-[4-benzyl-4-(propionylaminomethyl)piperid 1-yl]propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride

HRID 50065Notes

Reaction equation

HRID 50065 reaction equation
O.Cl.Cl.NCC1(CC2C=CC=CC=2)CCN(CCCC2(C3C=CC([Cl:35])=C(Cl)C=3)CCCN([C:21](=[O:28])[C:22]3C=CC=C[CH:23]=3)C2)CC1.[NH2:44][CH2:45][C:46]1([CH2:77][C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][CH2:54][C:55]2([C:69]3[CH:74]=[CH:73][C:72]([Cl:75])=[C:71]([Cl:76])[CH:70]=3)[CH2:60][CH2:59][CH2:58][N:57]([C:61](=[O:68])[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[CH2:56]2)[CH2:48][CH2:47]1.Cl.Cl.C(N(CC)CC)C.C(Cl)(=O)CC.Cl>C(Cl)Cl>[ClH:35].[C:61]([N:57]1[CH2:58][CH2:59][CH2:60][C:55]([CH2:54][CH2:53][CH2:52][N:49]2[CH2:50][CH2:51][C:46]([CH2:77][C:78]3[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=3)([CH2:45][NH:44][C:21](=[O:28])[CH2:22][CH3:23])[CH2:47][CH2:48]2)([C:69]2[CH:74]=[CH:73][C:72]([Cl:75])=[C:71]([Cl:76])[CH:70]=2)[CH2:56]1)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 1317216533-[3-[4-(Aminomethyl)-4-benzylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine dihydrochloride hemihydrate

Product 1

HCID 227418071-Benzoyl-3-[3-[4-benzyl-4-(propionylaminomethyl)piperid 1-yl]propyl]-3-(3,4-dichlorophenyl)piperidine hydrochlorideYield 121.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.6 g of the compound obtained in EXAMPLE 9 and 0.18 ml of triethylamine in 10 ml of DCM is cooled to 0° C., 0.1 ml of propionyl chloride is added dropwise and the mixture is stirred for 5 minutes. It is concentrated under vacuum, the residue is extracted with AcOEt, the organic phase is washed twice with water and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (9515; v/v) as the eluent. The product obtained is taken up with ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.37 g of the expected product.

Workup

  1. concentrationIt is concentrated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washthe organic phase is washed twice with water
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed
  9. filtrationis filtered off

Sources & evidence

ORD record
ord-957d016a49264fb2b36f9115c8e10356
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Reaction notes

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