Dichloromethane → HCID 178490147, compound

HRID 1733497Notes

Reaction equation

HRID 1733497 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH2:12][CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C(Cl)[Cl:31]>>[ClH:31].[ClH:31].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH2:12][CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 178490146HCID 178490146, compound

Product 1

HCID 178490147HCID 178490147, compound

Conditions

Temperature
10 °C

Procedure

A stirred mixture of 5 g of the product of Step A, 2.5 g of lithium aluminum hydride and 50 ml of tetrahydrofuran was refluxed for 90 minutes and was then cooled to 10° C. 100 ml of tetrahydrofuran containing 20% water and 100 ml of methylene chloride were added thereto and the mixture was filtered. The filtrate was evaported to dryness and the 4.7 g of yellow oil residue were dissolved in 30 ml of isopropanol. A solution of ethyl acetate saturated with hydrogen chloride was added thereto to adjust the pH to 1 and the mixture was vacuum filtered. The recovered product was washed with isopropanol to obtain 3 g of N-[2-(3-methoxyphenyl)-ethyl]-1H-imidazol-4-ethanamine dihydroch1oride in the form of brilliant colorless platelets melting at 195°-198° C.

Workup

  1. temperaturewas refluxed for 90 minutes
  2. filtrationthe mixture was filtered
  3. dissolutionthe 4.7 g of yellow oil residue were dissolved in 30 ml of isopropanol
  4. additionA solution of ethyl acetate saturated with hydrogen chloride was added
  5. filtrationfiltered
  6. washThe recovered product was washed with isopropanol

Sources & evidence

ORD record
ord-e48ebe66fb134eebac4117f9afaca0a3
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

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