Iodoethane → HCID 10030569, compound

HRID 358782Notes

Reaction equation

HRID 358782 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:37][CH3:38])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH:16]3[CH2:34][OH:35])=[O:14])=[CH:8][C:7]=2[CH:36]=1.[H-].[Na+].[CH2:41](I)[CH3:42]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:37][CH3:38])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=4)[CH2:17][CH:16]3[CH2:34][O:35][CH2:41][CH3:42])=[O:14])=[CH:8][C:7]=2[CH:36]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10436901HCID 10436901, compound

Product 1

HCID 10030569HCID 10030569, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)piperazine-2-methanol (500 mg) obtained by the method in Working Example 19 and N,N-dimethylformamide (3 ml) is cooled to 0° C., to which is added, in limited amounts, 60% oily sodium hydride (80 mg). The reaction mixture is stirred for 30 minutes and then cooled to -20° C., followed by adding thereto dropwise a mixture of ethyl iodide (200 mg) and N,N-dimethylformamide (1 ml). After stirring for 4 hours at -20° C., the reaction mixture is poured into ice-water, followed by extraction with methylene chloride. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate-hexane-methanol=50:45:5) to give 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -2-ethoxymethyl-4-(3,4,5trimethoxybenzyl)piperazine as a colorless oily product (420 mg). This product is dissolved in ethyl acetate and converted to its hydrochloride with 4N HCl (ethyl acetate solution). To the mixture is added ethyl ether, and left standing to give the hydrochloride as colorless crystals, m.p. 169-171° C.

Workup

  1. temperaturecooled to -20° C.
  2. additionby adding
  3. stirringAfter stirring for 4 hours at -20° C.
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate-hexane-methanol=50:45:5)

Sources & evidence

ORD record
ord-bc29f08f60564fd7ac0dc7659b9468b2
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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