Hydrochloric Acid → Hydrochloric Acid

HRID 1929639Notes

Reaction equation

HRID 1929639 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([I:15])[N:12]=[C:11]1[CH2:16][CH2:17][CH3:18])(C)(C)C.[ClH:20].O1CCOCC1>C(Cl)Cl>[I:15][C:13]1[N:12]=[C:11]([CH2:16][CH2:17][CH3:18])[N:10]([CH2:9][CH2:8][NH2:7])[CH:14]=1.[ClH:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66733914[2-(4-Iodo-2-propylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 667336172-(4-Iodo-2-propyl-imidazol-1-yl)-ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of [2-(4-iodo-2-propyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (6.110 g; 16.111 mmol) in DCM (100 ml) was added slowly 4N HCl in dioxane (80.5 ml; 322 mmol; 20 eq.). The resulting suspension was stirred at 0° C. for 15 min., and then at rt for 2 h. The volatiles were removed under reduced pressure, then under HV. The product 2-(4-iodo-2-propyl-imidazol-1-yl)-ethylamine was obtained as a colorless solid (5.620 g; 100%; presence of 2 eq. of HCl). LC-MS: tR=0.24 min.; [M+H]+=279.96 g/mol.

Workup

  1. waitat rt for 2 h
  2. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-88ed19b32cec4372b4dadcfc908633d5
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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