Hydrochloric Acid → 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid

HRID 2230576Notes

Reaction equation

HRID 2230576 reaction equation
C([N:11]1[CH2:15][CH2:14][C:13]([CH2:22][CH2:23][N:24]2[CH2:30][CH2:29][CH2:28][N:27]([C:31]3[N:35]([CH2:36][CH2:37][O:38][CH2:39][CH3:40])[C:34]4[CH:41]=[CH:42][CH:43]=[CH:44][C:33]=4[N:32]=3)[CH2:26][CH2:25]2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12]1)(OCC1C=CC=CC=1)=O.[Cl:45]CCl.Cl.O1CCOCC1>C(O)C.[Pd].[OH-].[Pd+2].[OH-].CCOCC>[ClH:45].[CH2:39]([O:38][CH2:37][CH2:36][N:35]1[C:34]2[CH:41]=[CH:42][CH:43]=[CH:44][C:33]=2[N:32]=[C:31]1[N:27]1[CH2:28][CH2:29][CH2:30][N:24]([CH2:23][CH2:22][C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][CH2:15][NH:11][CH2:12]2)[CH2:25][CH2:26]1)[CH3:40]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 184648341-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl) ethyl)-3-phenylpyrrolidine

Product 1

HCID 184649573-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Alternately, combine 1-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine (1.23 g, 2.06 mmol) in ethanol (20 mL). Add 10% palladium-on-carbon (0.2 g) and palladium hydroxide (0.2 g). Hydrogenate on a pressure apparatus at 50 psi. After 72 hours, remove the catalyst by filtration, and evaporate in vacuo to give a residue. Combine the residue and dichloromethane (50 mL). Add a solution of hydrochloric acid an dioxane (1.01 mL, 4 M, 4.0 mmol) and stir. After 3 hours, add dither ether (180 mL) to give a solid. Collect the solid by filtration and dry to give 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt: mp; 117-126° C.

Workup

  1. customremove the catalyst
  2. filtrationby filtration
  3. customevaporate in vacuo
  4. customto give a residue
  5. waitAfter 3 hours
  6. customto give a solid
  7. customCollect the solid
  8. filtrationby filtration
  9. customdry

Sources & evidence

ORD record
ord-f33357dfe2ec4289b658b8fa4518e6bf
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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