Hydrochloric Acid → HCID 21477592, compound

HRID 2293647Notes

Reaction equation

HRID 2293647 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH:5]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.C(N(CC)CC)C.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38].Cl>C(Cl)Cl.C(OCC)(=O)C.CCOCC>[ClH:27].[CH2:14]([CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH:5]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:4][NH:3][C:37](=[O:38])[O:39][CH2:40][CH3:41])[CH2:9][CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21477559HCID 21477559, compound

Product 1

HCID 21477592HCID 21477592, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

9.8 g of 1-amino-4-(4-benzylpiperidin-1-yl)-2-(3,4-dichlorophenyl)butane dihydrochloride and 6.7 g of triethylamine are dissolved in 200 ml of methylene chloride. 2.28 g of ethyl chloroformate are added dropwise to this solution at room temperature and the reaction mixture is left to stand for one hour at room temperature, with stirring. The reaction mixture is concentrated under vacuum and the residue is taken up in ethyl acetate/water and washed successively with a 5% solution of sodium hydroxide, water and a saturated solution of sodium chloride. The organic phase is dried over Na2SO4 and concentrated under vacuum to give a residue, which is chromatographed on silica gel using a 94/6 methylene chloride/methanol mixture as the eluent. Concentration of the pure fractions gives a residue, which is taken up in ethyl acetate. A solution of hydrogen chloride in ether is added to the ethyl acetate solution and the hydrochloride is filtered off.

Workup

  1. waitthe reaction mixture is left
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. washwashed successively with a 5% solution of sodium hydroxide, water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customis chromatographed on silica gel using a 94/6 methylene chloride/methanol mixture as the eluent
  8. customConcentration of the pure fractions gives a residue, which
  9. filtrationthe hydrochloride is filtered off

Sources & evidence

ORD record
ord-4f5cbda8927446b499fe9cb7ad48e0c0
Source dataset
uspto-grants-1997_11
Patent number
US05686609

Reaction notes

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