1,2-Dichloroethane → 4-[(5-Bromopyridin-3-yl)acetyl]morpholine

HRID 1892227노트

반응식

HRID 1892227 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(Cl)CCl.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CC1(C)C(C2C=NC(C)=C([N+]([O-])=O)C=2)=CCNC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

생성물 1

HCID 189859944-[(5-Bromopyridin-3-yl)acetyl]morpholine수율 95%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 673367223',3',6-Trimethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridine용매

실험 절차

To a solution of (5-bromopyridin-3-yl)acetic acid (1.00 g, 4.63 mmol) and morpholine (0.50 mL, 5.73 mmol) in DCM (50 mL) was added EDC (1.78 g, 9.30 mmol) and 1-hydroxybenzotriazole (1.25 g, 9.26 mmol). The reaction mixture was allowed to stir at rt for 50 min and then diluted with DCM (50 mL) and 1N HCl (100 mL). The organic solution was separated and discarded. The aqueous solution was neutralized with sat. aq. NaHCO3 (100 mL) and was extracted with DCM (3×50 mL). The organic solutions were combined, dried over MgSO4, filtered and concentrated to give 4-[(5-bromopyridin-3-yl)acetyl]morpholine (1.26 g, 4.40 mmol, 95%) as a light brown solid. LCMS (FA): Rt=1.11 min, m/z=287.0 (M+H).

후처리

  1. customThe organic solution was separated
  2. extractionwas extracted with DCM (3×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-359aa1526dc1435b83adfcedc197c6db
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507667B2

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