HCID 14699305, compound → HCID 14699306, compound

HRID 1165129Notes

Reaction equation

HRID 1165129 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1)=O>Cl>[CH:13]1([CH2:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH2:5])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1

Participants

3

Reactant 1

HCID 14699305HCID 14699305, compound

Product 1

HCID 14699306HCID 14699306, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 2,2-dimethyl-N-[2-(1,2,3,4-tetrahydro-1-isoquinolinyl)methylphenyl]propanamide (12.5 g) and 6N hydrochloric acid solution (240 ml) was refluxed for 101/2 hours and then allowed to stand overnight (about 16 hours) at room temperature. On cooling to room temperature a colorless solid separated. The mixture was decanted over crushed ice, water (300 ml) was added, and the mixture was basified with 50% sodium hydroxide solution. The turbid mixture was extracted thrice with 200 ml portions of CH2Cl2, and the combined dried (Na2SO4) organic phase was filtered and concentrated to an oil (10.15 g). On standing at 5° C. for 36 hours, a small amount of crystalline material formed. The oil was triturated with hexane and the crystalline material stirred into the oil, which resulted in complete solidification of the oil. The solid was collected by vacuum filtration, washed with hexane and dried in vacuo at room temperature to give 8.94 g (72%) of 2-[(1,2,3,4-tetrahydro-1-isoquinolinyl)methyl]benzenamine as a solid, m.p. 69°-71° C.

Workup

  1. custom(about 16 hours)
  2. customat room temperature
  3. customseparated
  4. customThe mixture was decanted
  5. customover crushed ice, water (300 ml)
  6. additionwas added
  7. extractionThe turbid mixture was extracted thrice with 200 ml portions of CH2Cl2
  8. dry with materialthe combined dried (Na2SO4) organic phase
  9. filtrationwas filtered
  10. concentrationconcentrated to an oil (10.15 g)
  11. waitOn standing at 5° C. for 36 hours
  12. customa small amount of crystalline material formed
  13. customThe oil was triturated with hexane
  14. customresulted in complete solidification of the oil
  15. filtrationThe solid was collected by vacuum filtration
  16. washwashed with hexane
  17. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-d3d192ab85d54878809d86754c8c76ea
Source dataset
uspto-grants-1990_03
Patent number
US04908361

Reaction notes

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