Hydrochloric Acid → 4-(iso-Propylcarbamoyl-methyl)-benzylamine

HRID 1191043Notes

Reaction equation

HRID 1191043 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:22])[NH:18][CH:19]([CH3:21])[CH3:20])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[CH:19]([NH:18][C:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH2:8])=[CH:15][CH:14]=1)=[O:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58495494N-(tert-Butoxycarbonyl)-4-(iso-propylcarbamoyl-methyl)-benzylamine

Product 1

HCID 584955244-(iso-Propylcarbamoyl-methyl)-benzylamineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve N-(tert-butoxycarbonyl)-4-(iso-propylcarbamoyl-methyl)-benzylamine (426 mg, 1.4 mmol) in DCM (5 mL). Add 4M hydrogen chloride in dioxane (3.5 mL, 14 mmol) and stir at room temperature for 1 h. Concentrate in vacuo and elute the compound through a SCX column to obtain the title compound as a white solid (281 mg, 98%). MS (ES+) m/z: 207 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. washelute the compound through a SCX column

Sources & evidence

ORD record
ord-016f8e5b4377489ca6e1ffd11c40d576
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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