1-Bromopropane → HCID 57489118, compound

HRID 2419515Notes

Reaction equation

HRID 2419515 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](=[O:15])[CH2:11][N:12]([CH3:14])[CH3:13].[CH2:20]([Mg]Br)[CH2:21][CH3:22].[Mg].C(Br)CC.[Cl-].[NH4+].[OH-].[Mg+2].[OH-]>CCOCC>[CH3:13][N:12]([CH3:14])[CH2:11][C:10]([C:6]1[N:5]([CH2:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[F:1])[CH:9]=[CH:8][CH:7]=1)([OH:15])[CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 6

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 73981Magnesium HydroxideHCID 5462224MagnesiumHCID 20391526HCID 20391526, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 57489118HCID 57489118, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 11.0 g of 1-(o-fluorobenzyl)-2-(dimethylaminoacetyl)pyrrole, free base of Example 3a, in ether is added dropwise to a stirring solution of n-propylmagnesium bromide which is prepared from 1.67 g of magnesium turnings and 8.4 g of n-propylbromide. The mixture is refluxed for 4 hours, allowed to cool, hydrolyzed with ice-water and treated with concentrated ammonium chloride solution to dissolve the magnesium hydroxide precipitated. The organic phase is separated and the aqueous phase extracted with ether and the organic phases are combined, washed with a 5% sodium bicarbonate solution and water and dried. Removal of the ether leaves a crude yellow oil which is distilled at 133°-137° C/0.08 mm gives a light yellow oil of 1-(dimethylamino)-2-[1-(o-fluorobenzyl)-2-pyrryl]-2-hydroxypentane.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. customprecipitated
  3. customThe organic phase is separated
  4. extractionthe aqueous phase extracted with ether
  5. washwashed with a 5% sodium bicarbonate solution and water
  6. customdried
  7. customRemoval of the ether
  8. customleaves a crude yellow oil which
  9. distillationis distilled at 133°-137° C/0.08 mm

Sources & evidence

ORD record
ord-3b2940939b7d4a919cc507e01645b406
Source dataset
uspto-grants-1978_08
Patent number
US04107074

Reaction notes

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