Hydroxyamine hydrochloride → 4-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldoxime

HRID 1457712노트

반응식

HRID 1457712 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:25][OH:26]>CO.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[N:25][OH:26])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 106393444-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldehyde

생성물 1

HCID 851794404-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldoxime수율 96.5%

시약·촉매·용매 1

HCID 22021344Pyridine methanol용매

실험 절차

A mixture of 4-(N-t-butyloxycarbonylpiperidin-4-ylmethoxy)benzaldehyde (3.16 g, 9.89 mmol) and hydroxylamine hydrochloride (1.27 g, 18.3 mmol) in 9:1 MeOH/pyridine (30 mL) was heated at reflux for 18 hours. The mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in EtOAc and washed with 0.1M HCl (3×), water, sat. CuSO4 (2×), water, sat. NaCl, dried (MgSO4) and concentrated, giving 3.19 g (96%) of the oxime; mp: 140.1°-141.8° C.; 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.48 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.14 (bs, 2H), 3.80 (d, J=6.2 Hz, 2H), 2.71 (bt, J=12.4 Hz, 2H), 1.95 (m, 1H), 1.80 (bd, J=12.4 Hz, 2H), 1.45 (s, 9H), 1.26 (m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 0.1M HCl (3×), water, sat. CuSO4 (2×), water, sat. NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0f0d63f0860344f4b7e38d5fb561d8c1
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849736

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