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Hydrochloric Acid → N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)-N-methylpropylamine

HRID 1956849
Notes
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Reaction equation

HRID 1956849 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:4][CH:3]=1.[CH2:20]=O.Cl>C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH3:20])=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 18349584N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)propylamine

Product 1

HCID 18349582N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)-N-methylpropylamine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
95 °C

Procedure

N-[2-(4-Chlorophenoxy)ethyl]-3-(imidazol-1-yl) propylamine (1.50 g) was added dropwise to 98% formic acid (1.0 ml) at 0° C. Formaldehyde (0.96 ml of a 37% aqueous solution) was added and the mixture heated at 95° C. for 6 hours. On cooling, concentrated hydrochloric acid (0.6 ml) was added. The mixture was evaporated to dryness and the residue dissolved in water, basified with 5M sodium hydroxide solution and extracted with ethyl acetate to give N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)-N-methylpropylamine as an oil.

Workup

  1. temperatureOn cooling
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-bd78d4739839483c9a0d115fc2794c07
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05780642

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes