Ethyl Bromide → HCID 20230196, compound

HRID 2290723Notes

Reaction equation

HRID 2290723 reaction equation
[Mg].[CH2:2](Br)[CH3:3].[F:5][C:6]1[CH:36]=[CH:35][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[Cl-].[NH4+]>CCOCC>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:26][CH2:27]3)=[CH:16][CH:17]=2)([OH:11])[CH2:2][CH3:3])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20230188(4-Fluorophenyl)[4-[3-[4-(phenylmethyl)-1-piperazinyl]propoxy]phenyl]methanone

Product 1

HCID 20230196HCID 20230196, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a Grignard reactant prepared from 2.4 g. of magnesium turnings and 11 g. of ethyl bromide in 40 ml. of dry ether a solution of 10.8 g. of 4-fluoro-4'-[3-(4-benzyl-piperazin-1-yl)-propoxy]-benzophenone in 200 ml. of dry ether is added dropwise, at -30° C. The reaction mixture is stirred at 0° C. for additional 30 minutes, and is then refluxed for one hour. After cooling the reaction mixture is poured onto a solution of ammonium chloride in ice water. The ethereal phase is separated. The aqueous phase is extracted with ether. The ethereal phases are combined and washed to neutral with water. After drying over anhydrous magnesium sulfate, the solution is evaporated in vacuo. The residue is crystallized from isopropyl ether. 5.3 g. of the end product are obtained, melting at 119° to 121° C.

Workup

  1. temperatureis then refluxed for one hour
  2. temperatureAfter cooling the reaction mixture
  3. customThe ethereal phase is separated
  4. extractionThe aqueous phase is extracted with ether
  5. washwashed to neutral with water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solution is evaporated in vacuo
  8. customThe residue is crystallized from isopropyl ether
  9. customof the end product are obtained

Sources & evidence

ORD record
ord-3197122314d1470da964e5b326643ad3
Source dataset
uspto-grants-1986_10
Patent number
US04618611

Reaction notes

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