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

HRID 637176Notes

Reaction equation

HRID 637176 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[CH2:11]([O:13][CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][C:34]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:38][CH2:37][NH:36][CH2:35]2)[CH2:27][CH2:26]1)[CH3:12].C([BH3-])#N.[Na+].Cl>CO.BrCOC1C(O)=CC=C(C)C=1.C(OCC)(=O)C>[CH3:2][CH:1]([N:36]1[CH2:37][CH2:38][C:34]([CH2:33][CH2:32][N:28]2[CH2:29][CH2:30][CH2:31][N:25]([C:17]3[N:16]([CH2:15][CH2:14][O:13][CH2:11][CH3:12])[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=3)[CH2:26][CH2:27]2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:35]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 5003444Sodium cyanoborohydrideHCID 184649573-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid

Product 1

HCID 184644841-(alpha-Methylbenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

Reagents, catalysts & solvents 3

HCID 86612474BromocreosolCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

According to the method of J. Am. Chem. Soc., 93, 2897 (1971), combine acetophenone (10 mmol) and 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine(R,R)-di-p-anisoyltartaric acid salt) (10 mmol) in methanol (100 mL). Add bromocreosol green (0.5% by weight in methanol, 1 drop). Add dropwise, a solution of sodium cyanoborohydride (10 mL, 1M in tetrahydrofuran, 10 mmol) and at the same time maintain the pH of the reaction mixture, as indicated by a yellow color for the indicator, by the addition of a 5 M solution of hydrochloric acid in methanol. When the reaction is complete, concentrate the reaction mixture in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. additionAdd dropwise
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto obtain a residue
  4. extractionextract with water
  5. customSeparate the layers
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-f32fe1178f4148a0b5518e662a0ca32b
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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