1,2,3,4-Tetrahydroisoquinoline → HCID 19887503, compound

HRID 654443Notes

Reaction equation

HRID 654443 reaction equation
C1C=CC(O[C:8](OC2C=CC=CC=2)=[N:9][C:10]#[N:11])=CC=1.[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1.[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:32][CH2:31]1>C(#N)C>[C:10]([NH:9][C:8]([N:20]1[CH2:21][CH2:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19]1)=[N:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:32][CH2:31]1)#[N:11]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 4158521-Benzyl-4-piperidylamineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 19887503HCID 19887503, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 mmole of diphenylcyanocarbonimidate (M.W. 238) in 15 ml of acetonitrile was added to 5 mmole of 1,2,3,4-tetrahydroisoquinoline at room temperature. After four hours of stirring at room temperature 5 mmole of 4-amino-1-benzyl piperidine was added to the reaction and stirring continued for an additional 2 hours. The mixture was then placed in a high pressure environment (20,000 psi) for 17 hours. The solution was evaporated and the residue was separated and purified by column chromatography (toulene:ethylacetate:triethylamine, 40:60:1).

Workup

  1. additionwas added to the reaction
  2. waitThe mixture was then placed in a high pressure environment (20,000 psi) for 17 hours
  3. customThe solution was evaporated
  4. customthe residue was separated
  5. custompurified by column chromatography (toulene:ethylacetate:triethylamine, 40:60:1)

Sources & evidence

ORD record
ord-f9f9a7459ea14c57b09078d1429e28fb
Source dataset
uspto-grants-1992_07
Patent number
US05132311

Reaction notes

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