Ammonium Chloride → 2-[[2-(3-Benzyloxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochloride

HRID 2264665

Reaction equation

HRID 2264665 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][NH:19][CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:26]1[CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27]1.[Cl-:33].[NH4+]>ClCCCl>[ClH:33].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][N:19]([CH2:31][CH:28]2[CH2:29][CH2:30][O:26][CH2:27]2)[CH2:20][C:21]([N:23]([CH3:24])[CH3:25])=[O:22])[CH:14]=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 4311764Sodium borohydrideHCID 595968562-[2-(3-benzyloxy-phenyl)-ethylamino]-N,N-dimethyl-acetamide

Product 1

HCID 665912062-[[2-(3-Benzyloxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.06 g (22 mmol) of NaBH4 were added portionwise to a mixture 2.9 g (9.3 mmol) of 2-[2-(3-benzyloxy-phenyl)-ethylamino]-N,N-dimethyl-acetamide, 1.28 ml (14.1 mmol) of tetrahydrofuran-3-carbaldehyde and 4 g of 4 Å molecular sieves in 130 ml of 1,2-dichloroethane. The reaction mixture was stirred at room temperature overnight. Aqueous ammonium chloride was added, the solvent was removed under vacuum, the residue was extracted with ethyl acetate and the organic phase was washed with an aqueous saturated solution of K2CO3. The solvent was removed under reduced pressure and the product was dissolved in anhydrous an hydrous hydrochloric acid in ethyl acetate. The solvent was removed and the product was triturated with diethyl ether. 3.2 g (80% yield) of the title compound were isolated as a yellow solid.

Workup

  1. customthe solvent was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate
  3. washthe organic phase was washed with an aqueous saturated solution of K2CO3
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe product was dissolved in anhydrous an hydrous hydrochloric acid in ethyl acetate
  6. customThe solvent was removed
  7. customthe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-fc38a04f6f0c439a9517ec76642b4e0e
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Linked notes

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