Hydrochloric Acid → HCID 13324722, compound

HRID 371492Notes

Reaction equation

HRID 371492 reaction equation
[N:1]1([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[ClH:18].[OH-].[Na+]>C1COCC1>[ClH:18].[N:1]1([C:10]2[CH:11]=[C:12]([CH2:13][NH2:14])[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13324749HCID 13324749, compound

Product 1

HCID 13324722HCID 13324722, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.1 g (32.3 mmole) of 3-(1-indolinyl)benzonitrile of Example 3a in 44 ml THF was added dropwise over 30 minutes to an ice cold solution of 129 ml (129 mmole, 4 equivalents) of 1M BH3.THF complex under nitrogen. After heating at reflux for 1 hour, the reaction mixture was cooled to 0°-5° C. and treated dropwise with 50 ml concentrated HCl. The resulting suspension was heated at reflux for 1 hour, permitted to stand at room temperature overnight (about 16 hours) and then made basic using 50% NaOH (60 ml). The reaction mixture was partitioned between water-CH2Cl2 (300 ml each) and the organic phase was washed with brine (300 ml), dried over MgSO4 and concentrated to give 8.9 g of crude free base. Conversion as in Example 1 to the HCl salt (ethanol/ethereal HCl) and recrystallization from hot acetonitrile-methanol afforded 2.86 g (34% overall) of 3-(1-indolinyl)benzenemethanamine hydrochloride, m.p. 170.5°-173.5° C.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1 hour
  3. temperaturethe reaction mixture was cooled to 0°-5° C.
  4. temperatureThe resulting suspension was heated
  5. temperatureat reflux for 1 hour
  6. custom(about 16 hours)
  7. customThe reaction mixture was partitioned between water-CH2Cl2 (300 ml each)
  8. washthe organic phase was washed with brine (300 ml)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customto give 8.9 g of crude free base
  12. customConversion as in Example 1 to the HCl salt (ethanol/ethereal HCl) and recrystallization from hot acetonitrile-methanol

Sources & evidence

ORD record
ord-a18da2cec5514509a01d72719c87de71
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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