Aniline → N-(1-Boc-piperidin-3-ylmethyl)aniline

HRID 479784

반응식

HRID 479784 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+]>CO.COC(OC)OC>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

6

반응물 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 99644481-Boc-piperidine-3-carboxaldehyde

생성물 1

HCID 12972131N-(1-Boc-piperidin-3-ylmethyl)aniline수율 79%

시약·촉매·용매 2

HCID 887Methanol용매HCID 9005Trimethyl orthoformate용매

실험 절차

To a solution of N-Boc-piperidin-3-yl-formaldehyde 3 (5.20 g, 24.4 mmol) in 50 mL of dry methanol and 50 mL of trimethylorthoformate was added aniline (2.50 g, 1.1 eq.), and the mixture was stirred at room temperature for 30 minutes. NaBH3CN (95%, 1.84 g, 1.1 eq.) was introduced in one portion, and the mixture was stirred at room temperature overnight. The mixture was quenched with 30 mL of aqueous potassium carbonate (sat.), then extracted with ethyl acetate (3×100 mL). The extracts were combined and washed with aqueous NaHCO3 (sat., 2×50 mL), brine (50 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was purified by a flash column chromatography (silica gel, hexane:ethyl acetate (1:1) to afford N-(1-Boc-piperidin-3-ylmethyl)-aniline 4 as white solid (5.60 g, 79%). IR (film, cm−1) 3520, 3263, 3004, 2976, 2932, 2854, 1688, 1589, 1521, 1482, 1422, 1365, 1267, 1243, 1175, 1150, 794, 709; 1H NMR (CDCl3, ppm) 7.20 (t, 2H, J=7.8 Hz), 6.72 (t, 1H, J=6.8 Hz), 6.63 (d, 2H, J=8.3 Hz), 4.00-3.78 (m, 3H), 3.07-2.70 (m, 4H), 2.00-1.20 (m, 5H), 1.48 (s, overlap, 9H).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with 30 mL of aqueous potassium carbonate (sat.)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washwashed with aqueous NaHCO3 (sat., 2×50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter the solvent was removed
  7. customthe remaining oily residue was purified by a flash column chromatography (silica gel, hexane:ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-5d6f55b461e94c8682b8177bdfe3dd03
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645980B1

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