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

HRID 1708451Notes

Reaction equation

HRID 1708451 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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); δ7.3-6.6 (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) .

Workup

  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); δ7.3-6.6 (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)

Sources & evidence

ORD record
ord-b532bc3bdba941ad81218ff532e226a1
Source dataset
uspto-grants-1994_10
Patent number
US05358971

Reaction notes

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