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

HRID 327587

Reaktionsgleichung

Reaktionsgleichung von HRID 327587
[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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d00fd4a5353845a58ddd8c8f0af6d863
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274003

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