Water → HCID 10405241, compound

HRID 1195165Notes

Reaction equation

HRID 1195165 reaction equation
C1(CO[NH:9][C:10]2([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:19][CH2:18][CH2:17][C:16]3[N:15]=[C:14]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:13]=[CH:12][C:11]2=3)C=CC=CC=1.B.O1CCCC1.O>O1CCCC1>[C:22]1([CH2:21][O:20][C:14]2[CH:13]=[CH:12][C:11]3[C:10]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([NH2:9])[CH2:19][CH2:18][CH2:17][C:16]=3[N:15]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 9981209HCID 9981209, compound

Product 1

HCID 10405241HCID 10405241, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5,6,7,8-Tetrahydro-N,2-bis(phenylmethoxy)-5-(phenylmethyl)-5-quinolinamine (40.0 g) in tetrahydrofuran (90 ml) was treated dropwise with borane-tetrahydrofuran complex (1M in tetrahydrofuran, 267 ml) at 0° C. The solution was heated under reflux for 3 hrs, cooled to 0° C. and water (30 ml) was added. The reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml) was added, and the mixture was heated under reflux for 8 hours. The mixture was cooled, acidified with conc hydrochloric acid, and washed with diethyl ether. The aqueous phase was basified with 20% potassium hydroxide solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated to afford 19.1 g (37.0%) of product.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml)
  4. additionwas added
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 8 hours
  7. temperatureThe mixture was cooled
  8. washwashed with diethyl ether
  9. extractionextracted with dichloromethane
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried over potassium carbonate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9a365647a1ec42c9aa257ae4e81755d5
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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