Ammonium Chloride → HCID 60108778, compound

HRID 1005655Notes

Reaction equation

HRID 1005655 reaction equation
[C:1]([Mg]Br)([CH3:3])=[CH2:2].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([N+]([O-])=O)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[Cl-].[NH4+:29]>C1COCC1>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:20]=2[NH:29][C:1]([CH3:3])=[CH:2]3)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33806961-Boc-4-(4-Nitrophenyl)piperazineHCID 178456138HCID 178456138, compound

Product 1

HCID 60108778HCID 60108778, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Isopropenyl magnesium bromide (234 mL of a 0.5 M solution in THF, 117 mmol) was slowly added to a −40° C. solution of 4-(4-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (12 g, 39 mmol) in 200 mL of THF and the resulting mixture was stirred at −40° C. for 20 min. Saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried (sodium sulfate) and evaporated. Silica gel chromatography (20% ethyl acetate-hexane) afforded 4.8 g of 4-(2-methyl-1H-indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (21) as an oil, mass spec, M+ 315.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-d6b0da9c1e964d238cca12a3aa5f172c
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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