4-Piperidinecarboxylic acid → 1-(3-Bromo-5-cyanophenyl)piperidine-4-carboxylic acid

HRID 1473863

반응식

HRID 1473863 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](F)[CH:9]=1)[C:5]#[N:6].[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.CN(C)C(=O)C>CCOC(C)=O.O>[Br:1][C:2]1[CH:9]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]2)[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1

참가 물질

7

반응물 4

HCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 27833303-Bromo-5-fluorobenzonitrile

생성물 1

HCID 595881891-(3-Bromo-5-cyanophenyl)piperidine-4-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

A mixture of 3-bromo-5-fluorobenzonitrile (1.6 g, 7.8 mmol), piperidine-4-carboxylic acid (2.6 g, 12.0 mmol), triethylamine (4.0 mL, 28.5 mmol) and N,N-dimethylacetamide (1.5 mL) in a sealed tube was heated to 130° C. for 48 hr. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, dried (MgSO4), and concentrated to give a crude reside which was purified by chromatography on silica gel (CH2Cl2/MeOH) to afford 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylic acid.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a crude reside which
  5. customwas purified by chromatography on silica gel (CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-d29d1020a44143528ce1a4ffac2d4325
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018205B2

연결된 노트

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