Hydrochloric Acid → 3-(2-(4-(1-(2-Ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

HRID 323377Notes

Reaction equation

HRID 323377 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28]3[N:32]([CH2:33][CH2:34][O:35][CH2:36][CH3:37])[C:31]4[CH:38]=[CH:39][CH:40]=[CH:41][C:30]=4[N:29]=3)[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>ClCCl>[CH2:36]([O:35][CH2:34][CH2:33][N:32]1[C:31]2[CH:38]=[CH:39][CH:40]=[CH:41][C:30]=2[N:29]=[C:28]1[NH:27][CH:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][C:10]2([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:22][CH2:23]1)[CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 539562491-(t-butoxycarbonyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Product 1

HCID 220091003-(2-(4-(1-(2-Ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (10 mmol) and a solution of hydrochloric acid in dioxane (10 mL. 4 M, 40 mmol) in dichloromethane (150 mL). After 24 hours, evaporate in vacuo to give a residue. Partition the residue between with dichloromethane (300 mL) and a saturated aqueous solution of sodium bicarbonate. Separate the organic layer and extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. customPartition the residue between with dichloromethane (300 mL)
  4. customSeparate the organic layer
  5. extractionextract with brine
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-9576c604de9a40249475245cd3768b94
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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