Sodium Bicarbonate → HCID 22111019, compound

HRID 565699Notes

Reaction equation

HRID 565699 reaction equation
[C:1]1([CH:7]([NH:14][CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3([CH3:44])[CH2:28][C:27]4[C:29]([CH3:43])=[C:30]([NH:35]C(=O)OC(C)(C)C)[C:31]([CH3:34])=[C:32]([CH3:33])[C:26]=4[O:25]3)[CH2:19][CH2:18]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(O)C.C(=O)([O-])O.[Na+]>C(O)C>[NH2:35][C:30]1[C:31]([CH3:34])=[C:32]([CH3:33])[C:26]2[O:25][C:24]([CH2:23][N:20]3[CH2:21][CH2:22][CH:17]([CH2:16][CH2:15][NH:14][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:18][CH2:19]3)([CH3:44])[CH2:28][C:27]=2[C:29]=1[CH3:43]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 86756222HCID 86756222, compound

Product 1

HCID 22111019HCID 22111019, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl [2-[[4-[2-[(diphenylmethyl)amino]ethyl]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate (1.6 g) in ethanol (3 mL) was added 10 mL of 4N-HCl/ethanol and the mixture was stirred at room temperature for 15 hours. This reaction mixture was made basic with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 1.3 g of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(diphenylmethyl)-4-piperidineethylamine. Yield 97%. This product was treated with 4N-HCl solution in ethanol and the resulting trihydrochloride was recrystallized from ethanol/diethyl ether to provide 1.3 g of the title compound. Yield 76%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-f0cc8b2e4f2e493b964f0af6d28660e8
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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