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

HRID 327585

반응식

HRID 327585 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>CCOCC>[CH2:1]([N: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)[CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH3:3]

참가 물질

5

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A mixture of 2-(N-n-propylamino)-5-methoxytetralin (7.0 g, 0 0319 mol; prepared according to J. Chem. Soc., 1965, pp. 26-36), phenoxyacetic acid (4.86 g, 0.0319 mol), and borane trimethylamine complex (2.33 g, 0.0319 mol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting oil was subjected to flash chromatography (silica; 9:1 pet ether/EtOAc) and product was isolated: NMR of the free base (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). The free base thus isolated was converted to hydrochloride salt by the addition of dry ether-HCL.

후처리

  1. customprepared
  2. customThe cooled reaction mixture
  3. extractionwas extracted with NaHCO3
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customproduct was isolated
  8. customThe free base thus isolated

출처 및 근거

ORD 기록
ord-adb00b0532464acfa885f84695ff13dc
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274003

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