Benzyl Chloride → HCID 10161821, compound

HRID 2065974Notes

Reaction equation

HRID 2065974 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) is added at 23° C. to a solution containing (1R)-1-(1-benzyl-4-tert-butyl-1H-imidazol-2-yl)-2-(1H-indol-3-yl)ethanamine (0.7 g; 0.002 mol; prepared under experimental conditions similar to those previously and using suitable starting reagents and reaction products) in 15 ml of acetonitrile. The mixture is stirred for one hour at 23° C. then benzyl chloride (0.23 ml; 0.002 mol) is added. Stirring is maintained for 16 hours. The reaction mixture is concentrated using a rotary evaporator and the oil obtained is taken up in ethyl acetate and water. The aqueous phase is extracted with ethyl acetate and washed with water then with a saturated solution of sodium chloride. The solvents are evaporated off under vacuum. After purification on a silica column (eluent: AE-heptane/7-3), a deep beige-coloured solid is obtained in the form of a paste (yield of 5%). Free base. Melting point: 60-62° C.

Workup

  1. customprepared under experimental conditions similar to those previously and
  2. stirringStirring
  3. temperatureis maintained for 16 hours
  4. concentrationThe reaction mixture is concentrated
  5. customa rotary evaporator
  6. customthe oil obtained
  7. extractionThe aqueous phase is extracted with ethyl acetate
  8. washwashed with water
  9. customThe solvents are evaporated off under vacuum
  10. customAfter purification on a silica column (eluent: AE-heptane/7-3)
  11. customa deep beige-coloured solid is obtained in the form of a paste (yield of 5%)

Sources & evidence

ORD record
ord-f3b193be16e24ae39cb91e2802f631a0
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Reaction notes

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