Phenoxyacetic Acid → 2-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

HRID 327587

반응식

HRID 327587 반응식
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[CH2:6]1)[CH2:2][CH3:3].[O:17]([CH2:24][C:25](O)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[B-][N+](C)(C)C>>[CH3:16][O:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH2:14][CH:5]([N:4]([CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:1][CH2:2][CH3:3])[CH2:6]2

참가 물질

4

반응물 3

HCID 19188Phenoxyacetic AcidHCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 102425482-Propylamino-5-methoxytetralin

생성물 1

HCID 152288502-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

실험 절차

A mixture of (-)-2-(N-n-propylamino)-5-methoxytetralin (80 mg, 31.9 mmol; prepared according to J. Chem. Soc., 1965, pp 26-36), phenoxyacetic acid (166 mg, 109.4 mmol) and borane trimethylamine complex (80 mg, 109.4 mmol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSo4, filtered and concentrated. The resulting oil was subjected to flash chromatography (Silica: 9:1 pet ether/EtOAc) and product was isolated with characteristic peaks at: NMR (300 MHz, CDCl3); δ 7.3-6.6 (m, 8H), 4.0(t,2H), 3.7(S,3H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4(m,3H) 0.9(t,3H).

후처리

  1. customThe cooled reaction mixture
  2. extractionwas extracted with NaHCO3
  3. customthe organic layer was dried over MgSo4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customproduct was isolated with characteristic peaks at: NMR (300 MHz, CDCl3); δ 7.3-6.6 (m, 8H), 4.0(t,2H), 3.7(S,3H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4(m,3H) 0.9(t,3H)

출처 및 근거

ORD 기록
ord-d00fd4a5353845a58ddd8c8f0af6d863
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274003

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