Hydrochloric Acid → 3'-Hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide

HRID 2367737Notes

Reaction equation

HRID 2367737 reaction equation
C(O[C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:28])[NH:16][C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([CH3:27])[CH2:24]3)=[CH:19][CH:18]=2)[CH:10]=1)(C)(C)C.[ClH:30].[O:31]1[CH2:36][CH2:35]OCC1.[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)Cl.CCOCC>[CH3:27][N:23]1[CH2:22][CH2:21][C:20]2[C:25](=[CH:26][C:17]([NH:16][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[CH2:8][NH:7][C:6]([C:39]3[CH:38]=[CH:37][C:42]([C:9]4[CH:10]=[CH:11][CH:35]=[C:36]([OH:31])[CH:8]=4)=[CH:41][CH:40]=3)=[O:29])=[O:28])=[CH:18][CH:19]=2)[CH2:24]1.[ClH:30].[ClH:30].[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][N:23]([CH3:27])[CH2:24]2)=[CH:19][CH:18]=1)=[O:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8058Hexane2×HCID 312751,4-DioxaneHCID 66656233[3-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester

Product 2

HCID 566003433'-Hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamideHCID 666490723-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester (6.35 g, 15.6 mmol) in anhydrous DCM (250 mL) at rt add 4M HCl in 1,4-dioxane (58.4 mL, 233.6 mmol) and stir the reaction at rt for 24 h. Dilute the solid suspension with Et2O (500 mL) and hexane (800 mL), stir vigorously for 20 min then filter and wash with Et2O then hexane to afford the desired product 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride as a hydroscopic solid (5.68 g, 14.7 mmol).

Workup

  1. customthe reaction at rt for 24 h
  2. stirringstir vigorously for 20 min
  3. filtrationthen filter
  4. washwash with Et2O

Sources & evidence

ORD record
ord-493bf1b0db74460397d6b3dde3fa9b6f
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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