Hydrochloric Acid → HCID 13324746, compound

HRID 544141Notes

Reaction equation

HRID 544141 reaction equation
[N:1]1([C:10]2[CH:11]=[C:12]([CH2:16][NH:17][C:18](=O)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=[CH:14][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[ClH:33]>C1COCC1>[ClH:33].[N:1]1([C:10]2[CH:11]=[C:12]([CH2:16][NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=[CH:14][CH:15]=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 13408840HCID 13408840, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13324746HCID 13324746, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.53 g (45.35 mmole) of 3-(1-indolinyl)-N-phenylacetylbenzenemethanamine of Example 12 in 65 ml distilled THF was added dropwise over 30 minutes to an ice-salt cooled, rapidly stirred slurry of 10.44 g (275.1 mmole, 6.07 equivalents) LiAlH4 in 275 ml distilled THF under nitrogen. After warming to room temperature and stirring for 2 hours, the reaction mixture was heated under reflux for 19 hours and then quenched at 0° C. with 20 ml ice water-THF (1:1), 10 ml 10% NaOH, and 30 ml water. The salts were filtered, washed with CHCl3 and the filtrate was concentrated. The residue was dissolved in CHCl3, washed with brine, dried over Na2SO4, and concentrated to give 11.70 g (78.6%) of crude free base. Conversion to the HCl salt (ether/ethereal HCl) using the procedure of Example 1 gave 11.43 g (69.1%). Recrystallization from hot absolute ethanol gave 2.88 g (17.4% overall) of 3-(1-indolinyl)-N-(2-phenylethyl)benzenemethanamine hydrochloride, m.p. 188°-190° C.

Workup

  1. temperaturecooled
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 19 hours
  4. customquenched at 0° C. with 20 ml ice water-THF (1:1), 10 ml 10% NaOH, and 30 ml water
  5. filtrationThe salts were filtered
  6. washwashed with CHCl3
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe residue was dissolved in CHCl3
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customto give 11.70 g (78.6%) of crude free base
  13. customgave 11.43 g (69.1%)
  14. customRecrystallization from hot absolute ethanol

Sources & evidence

ORD record
ord-bf1cf3ddcf044b0e9906a631d0b3a930
Source dataset
uspto-grants-1984_05
Patent number
US04448784

Reaction notes

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