Water → 2-Benzyloxy-5,6,7,8-tetrahydro-quinolin-5-ylamine

HRID 1821095Notes

Reaction equation

HRID 1821095 reaction equation
C(O[NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]=[C:14]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=[CH:12][C:11]1=2)C1C=CC=CC=1.B.O>C1COCC1>[CH2:21]([O:20][C:14]1[CH:13]=[CH:12][C:11]2[CH:10]([NH2:9])[CH2:19][CH2:18][CH2:17][C:16]=2[N:15]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 19026180HCID 19026180, compound

Product 1

HCID 99213182-Benzyloxy-5,6,7,8-tetrahydro-quinolin-5-ylamineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of O-benzyl-N-(2-benzyloxy-5,6,7,8-tetrahydro-quinolin-5-yl)-hydroxylamine (51.0 g, 142 mmoL) dissolved in dry THF (65 mL) was cooled in ice-water bath under nitrogen. Borane (1.0 M in THF, 427 mL) was added dropwise in 30 min via an addition funnel. The reaction was allowed to warm up to room temperature and stirred for overnight. The mixture was then heated to reflux. After 2 h, the heating was stopped and the reaction was allowed to cool to room temperature. Water (120 mL) was added dropwise via an addition funnel. The mixture was then concentrated, and 20% aqueous sodium hydroxide (200 mL) was added. The resulting mixture was heated to reflux for 2 h. The reaction was allowed to cool to room temperature, and extracted with methylene chloride (×3). The combined methylene chloride extract was dried, filtered and concentrated. Purification by column chromatography on silica gel with 20% methanol/1% ammonium hydroxide/methylene chloride provided the desired product (32.0 g, 89%) as colorless oil.

Workup

  1. temperatureThe mixture was then heated to reflux
  2. waitAfter 2 h
  3. temperatureto cool to room temperature
  4. concentrationThe mixture was then concentrated
  5. addition20% aqueous sodium hydroxide (200 mL) was added
  6. temperatureThe resulting mixture was heated
  7. temperatureto reflux for 2 h
  8. temperatureto cool to room temperature
  9. extractionextracted with methylene chloride (×3)
  10. extractionThe combined methylene chloride extract
  11. customwas dried
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customPurification by column chromatography on silica gel with 20% methanol/1% ammonium hydroxide/methylene chloride

Sources & evidence

ORD record
ord-3c6206aae1034fabb2818b092cd23a96
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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