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

HRID 1261454
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HRID 1261454 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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 wasdissolved in anhydrous anhydrous 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.

후처리

  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. customThe solvent was removed
  6. customthe product was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-913114f29a314f03a6c724a676437416
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08470877B2

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