Formaldehyde → HCID 10269672, 화합물

HRID 412999노트

반응식

HRID 412999 반응식
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([CH2:21][CH2:22][NH:23][CH3:24])=[C:4]1[CH3:25].C=O.[C:28]([BH3-])#N.[Na+]>C(#N)C>[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([CH2:21][CH2:22][N:23]([CH3:28])[CH3:24])=[C:4]1[CH3:25]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 185227762-[1,2-dimethyl-5-(phenylsulfonyl)-1H-indol-3-yl]-N-methylethanamine hydrochloride

생성물 1

HCID 10269672HCID 10269672, 화합물수율 24.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2-[1,2-dimethyl-5-(phenylsulfonyl)-1H-indol-3-yl]-N-methylethanamine hydrochloride (0.34 g, 0.91 mmol) and formaldehyde (37%, 1.4 mL, 18.80 mmol) in acetonitrile was treated with sodium cyanoborohydride (0.92 g, 14.69 mmol) in portions. The reaction was stirred at room temperature for 2.5 days. The reaction mixture was concentrated in vacuo and the residue partitioned between CHCl3 and NH4OH. The layers were separated and the aqueous layer was extracted with CHCl3. The organic layers were combined, washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and subjected to column chromatography (silica gel, 75% EtOAc/hexane) to give 0.08 g (23%) of white solid as the title compound: mp 169.6-171.9° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.07 (s, 1H), 7.93-7.91 (m, 2H), 7.63-7.55 (m, 5H), 3.67 (s, 3H), 2.86-2.82 (m, 2H), 2.41-2.37 (m, 2H), 2.36 (s, 3H), 2.24 (s, 6H); 13C NMR (100 MHz, DMSO-d6) δ 142.8, 137.9, 136.8, 132.7, 130.3, 129.3, 126.8, 126.7, 118.7, 118.0, 110.2, 110.0, 59.9, 44.9, 29.7, 21.8, 9.9; IR (diffuse reflectance) 2936, 2776, 2760, 1482, 1449, 1377, 1303, 1285, 1153, 1143, 1094, 729 (s), 687, 651, 619 cm−1; HRMS (FAB) calcd for C20H24N2O2S+H 357.1637, found 357.1649; Anal. Calcd for C20H24N2O2S: C, 65.72; H, 6.88; N, 7.66. Found: C, 65.52; H, 6.71; N, 7.73.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between CHCl3 and NH4OH
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CHCl3
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-413a45302a4e44778c85c681dadd116a
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06565829B2

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