[4-(1-methyl-1H-imidazol-2-yl)-benzyl]-carbamic acid tert-butyl ester → (4-(1-Methyl-1H-imidazol-2-yl)phenyl)methanamine

HRID 911282Notes

Reaction equation

HRID 911282 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=2)=[CH:11][CH:10]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:20][N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH2:7])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 57656293[4-(1-methyl-1H-imidazol-2-yl)-benzyl]-carbamic acid tert-butyl ester

Product 1

HCID 57656174(4-(1-Methyl-1H-imidazol-2-yl)phenyl)methanamineYield 75.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve [4-(1-methyl-1H-imidazol-2-yl)-benzyl]-carbamic acid tert-butyl ester (500 mg, 1.7 mmol) in DCM (20 mL) and trifluoroacetic acid (5 mL). Stir the mixture for 1 h at ambient temperature. Concentrate in vacuo and purify by SCX chromatography to obtain the title compound (240 mg, 74%). MS (ES+) m/z: 188 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-c2b2c56fce434230879b348b5895831a
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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