Benzyl Alcohol → HCID 21254098, compound

HRID 1531551Notes

Reaction equation

HRID 1531551 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=1)=[C:14]2[CH2:28][CH2:29][N:30]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.C(O)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:44]([N:30]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)[CH2:29][CH2:28][C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([NH2:10])[CH:12]=2)[NH:16][C:15]=1[C:20]1[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 70226998HCID 70226998, compound

Product 1

HCID 21254098HCID 21254098, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a solution of [3-(2-{benzyl-[4-(4-nitrophenyl)butyl]amino}ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]carbamic acid benzyl ester (500 mg in 25 mL dry methylene chloride) was added 0.50 mL anisole followed by 0.035 mL benzyl alcohol and the mixture stirred at room temperature. Then, 2.94 mL of a 1M solution of aluminum chloride in nitrobenzene was added dropwise. After 11.5 hours, the reaction was cooled to 0° C. and quenched by the addition of saturated aqueous sodium bicarbonate and partitioned between ethyl acetate and aqueous sodium potassium tartarate. The organic portion was washed with additional tartarate solution and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 97:3) gave the title compound (354 mg).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the addition of saturated aqueous sodium bicarbonate
  3. custompartitioned between ethyl acetate and aqueous sodium potassium tartarate
  4. washThe organic portion was washed with additional tartarate solution
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 97:3)

Sources & evidence

ORD record
ord-26ddcfd87f1e4f0f8d880e9a4e1301f7
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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