Hydrochloric Acid → HCID 13324722, compound

HRID 544136Notes

Reaction equation

HRID 544136 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 1 M 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
  8. washCH2Cl2 (300 ml each) and the 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-89cd1bcc0cca4e0cbf4876119c55ab12
Source dataset
uspto-grants-1984_05
Patent number
US04448784

Reaction notes

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