Formaldehyde → HCID 45117639, 화합물

HRID 1057166

반응식

HRID 1057166 반응식
[C:1]([BH3-])#N.[Na+].Cl.[S:6]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]=2[CH:8]=[CH:7]1.C=O>ClCCl>[CH3:1][N:11]1[CH2:12][CH2:13][C:14]2[S:6][CH:7]=[CH:8][C:9]=2[CH2:10]1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chloride

생성물 1

HCID 45117639HCID 45117639, 화합물수율 33%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Sodium cyanoborohydride (10 g, 160 mmol) was slowly added to a mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (7.0 g, 40.0 mmol) and formaldehyde (35% in water, 10 mL) in dichloromethane (100 mL) at room temperature. The resulting mixture was stirred at room temperature for 16 h. Work-up: the reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL). The organic layer was separated, washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5˜1:1) to afford the title compound as a white solids (2.0 g, 33%). 1H NMR (DMSO-d6, 400 MHz): δ 7.26 (d, 1H), 6.77 (d, 1H), 3.37 (s, 2H), 2.80-2.77 (m, 2H), 2.64-2.60 (m, 2H), 2.34 (s, 3H).

후처리

  1. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5˜1:1)

출처 및 근거

ORD 기록
ord-a44775a76b5d412ebcf6c2f5b4c94991
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

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