Ammonium Chloride → HCID 67588734, compound

HRID 863541Notes

Reaction equation

HRID 863541 reaction equation
CON(C)[C:4]([C@H:6]1[CH2:18][CH2:17][N:9]2[C:10]3[C:15]([CH:16]=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:5].[CH:20]([Mg]Cl)([CH3:22])[CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[C:8]1[CH2:7][C@@H:6]([C:4]([CH:20]([CH3:22])[CH3:21])=[O:5])[CH2:18][CH2:17][N:9]12

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22882815HCID 22882815, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67588734HCID 67588734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 10.0 g (38.7 mmol) of 6,7,8,9-tetrahydro-N-methoxy-N-methyl-pyrido[1,2-a]indole-8(S)-carboxamide in 250 ml of tetrahydrofuran was treated dropwise at 0° C. with 60 ml (120 mmol) of a 2M solution of isopropylmagnesium chloride in tetrahydrofuran. The mixture was stirred at room temperature for 18 hours and poured into 250 ml of saturated ammonium chloride solution. The aqueous phase was washed four times with 100 ml of diethyl ether each time and the combined ethereal extracts were washed with 200 ml of brine, dried over magnesium sulfate and evaporated to dryness. The product was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (1:3) for the elution to give 4.4 g of isopropyl 6,7,8,9-tetrahydropyrido[1,2-a]indol-8(S)-yl ketone as a white solid of melting point 78°-79° C.

Workup

  1. washThe aqueous phase was washed four times with 100 ml of diethyl ether each time
  2. washthe combined ethereal extracts were washed with 200 ml of brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe product was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-3db7dd79b4e942b7bae22663be0e59f6
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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