Ammonium Chloride → HCID 11316124, compound

HRID 1533080Notes

Reaction equation

HRID 1533080 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH:8]2[CH2:24][CH:25]=[O:26])=[CH:4][CH:3]=1.[CH3:29][Mg]Br.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH:8]2[CH2:24][CH:25]([OH:26])[CH3:29])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22264737HCID 22264737, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 11316124HCID 11316124, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-fluorobenzyl)-1-((4-chlorophenoxy)methyl)carbonyl-3-((formyl)methyl)piperazine (0.31 g, 0.77 mmol) in anhydrous THF (20 mL) was added methyl magnesium bromide (0.26 mL, 0.77 mmol, 3.0 M solution in ether). The resultant mixture was stirred overnight at ambient temperature. At that time the mixture was poured into 5% aqueous NH4Cl solution and extracted with two portions of ether. The combined organic extracts were washed with brine, then dried over MgSO4, filtered and concentrated in vacuo to afford a yellow oil. Purification by flash column chromatography on silica gel afforded 0.29 g of 4-(4-fluorobenzyl)-1-((4-chlorophenoxy)methyl)carbonyl-3-(2-hydroxypropyl)piperazine, as a clear, colorless oil, which was converted to its hydrochloride salt; NMR (CDCl3) 7.6 (m, 2), 7.2 (m, 4), 6.9 (m, 2), 4.7 (m, 2), 4.4-3.0 (m, 10), 2.4-1.4 (m, 2), 1.3-1.0 (m, 3) ppm.

Workup

  1. extractionextracted with two portions of ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow oil
  7. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-3418e5bd47f94a789b86384c8c5b997b
Source dataset
uspto-grants-2001_03
Patent number
US06207665B1

Reaction notes

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