Sulfuric Acid → HCID 10206976, compound

HRID 1282006Notes

Reaction equation

HRID 1282006 reaction equation
[Cl:1][C:2]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][N:27]3C(=O)C4=CC=CC=C4C3=O)[CH2:18][CH2:17]2)[CH2:6]1.NN.OS(O)(=O)=O>C(O)C>[Cl:1][C:2]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH2:18][CH2:17]2)[CH2:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9321HydrazineHCID 12972321HCID 12972321, compound

Product 1

HCID 10206976HCID 10206976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.2 g (0.32 mmol) of 1-(2,4-dichlorobenzyl)-3-(S)-(4-(3-phthalimidopropyloxymethyl)piperidinylmethyl)-4-(S)-(3-thienyl)pyrrolidine (Example 20) and 0.2 mL (6.4 mmol) of hydrazine in 2 mL of ethanol was heated at 60° C. for 5 h. To the reaction mixture was added 20 mL of 10% H2SO4 and the mixture was extracted three times with ethyl acetate. The aqueous layer was brought to pH=12 by addition of 15% NaOH and extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and the filtrate was concentrated to give the title compound. Mass Spectrum (ESI) m/e=496 (M+1 35Cl, 35Cl), 498 (M+1 35Cl, 37Cl), and 500 (M+1 37Cl, 37Cl). [α]D=+14.9 (c=0.875, CHCl3).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. additionThe aqueous layer was brought to pH=12 by addition of 15% NaOH
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8f5be84256a74134a5919d3ab7516513
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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