Benzyl Chloride → HCID 10161821, compound

HRID 230388Notes

Reaction equation

HRID 230388 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:17]=[C:16]1[C@H:24]([NH2:35])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:36](Cl)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(#N)C.C(OCC)(=O)C.O>[CH2:36]([NH:35][C@@H:24]([C:16]1[N:15]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:19]=[C:18]([C:20]([CH3:22])([CH3:23])[CH3:21])[N:17]=1)[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 67214147HCID 67214147, compound

Product 1

HCID 10161821HCID 10161821, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

Triethylamine (0.83 ml; 0.006 mol) was added at about 23° C. to a solution of (1R)-1-(1-benzyl-4-tert-butyl-1H-imidazol-2-yl)-2-(1H-indol-3-yl)ethanamine (0.7 g; 0.002 mol; prepared according to experimental conditions analogous to the preceding examples and using the appropriate starting compounds and reaction products) in 15 ml acetonitrile. The mixture was agitated about one hour at about 23° C. and benzyl chloride (0.23 ml; 0.002 mol) was added. Agitation was maintained for about 16 hours. The reaction mixture was concentrated using a rotative evaporator and the oil obtained was taken up in ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and washed with water and then with a saturated solution of sodium chloride. The solvents were evaporated under vacuum. After purification over a silica column (eluent: ethyl acetate-heptane/7-3), a strong beige solid was obtained in the form of a glue (yield of 5%). Free base. Melting point: 60-62° C. MH+=463.3.

Workup

  1. customprepared
  2. temperatureAgitation was maintained for about 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. customa rotative evaporator
  5. customthe oil obtained
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washwashed with water
  8. customThe solvents were evaporated under vacuum
  9. customAfter purification over a silica column (eluent: ethyl acetate-heptane/7-3)
  10. customa strong beige solid was obtained in the form of a glue (yield of 5%)

Sources & evidence

ORD record
ord-5552549c3a7244c2a7f25a78047820a8
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Reaction notes

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