Hydrochloric Acid → HCID 9877750, compound

HRID 2307277Notes

Reaction equation

HRID 2307277 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1.[OH-].[Na+]>CCOC(C)=O.O>[N:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 122884-ChloropyridineHCID 14798Sodium Hydroxide

Product 1

HCID 9877750HCID 9877750, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-pyridine 1:1 hydrochloride (24.5 g, 163 mmol) and 1,2,3,4-tetrahydro-isoquinoline (65.3 g, 490 mmol) was slowly heated to 150° C. After 30 min the reaction mixture was cooled to rt, H2O (700 ml) and 2N NaOH (82 ml) was added followed by extraction with AcOEt (5 times 300 ml). The combined organic phases were dried (Na2SO4), and the solvent was evaporated. After trituration with pentane and recrystallization the title compound (30.2 g, 88%) was obtained as a light brown crystalline material. Mp. 95-96° C. (AcOEt), MS: m/e=210 (M+).

Workup

  1. temperatureAfter 30 min the reaction mixture was cooled to rt
  2. extractionfollowed by extraction with AcOEt (5 times 300 ml)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customAfter trituration with pentane and recrystallization the title compound (30.2 g, 88%)
  6. customwas obtained as a light brown crystalline material

Sources & evidence

ORD record
ord-234cbb43bd6a4e1697e53ac7c0a678be
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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