Ammonium → HCID 21523490, compound

HRID 918198Notes

Reaction equation

HRID 918198 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][N:4]2[C:3]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[N:2]1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+].[NH4+]>CCOCC>[C:12]1([C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:3]2[N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]3[CH2:1][N:2]=2)[OH:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 25517Ammonium ChlorideHCID 71398802(1,5,6,7,8,8a-Hexahydroimidazo[1,5-a]pyridin-3-yl)(phenyl)methanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 21523490HCID 21523490, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The oil from Example 2 was dissolved in dried ether (25 ml.) and immediately added to phenylmagnesium bromide (prepared from 1.23g. magnesium and 8.00g. bromobenzene) in 150ml. dried ether. The mixture was stirred at room temperature for 16 hours. It was then poured on to a mixture of ammonium chloride (2.7g.) and ice and basified with ammonium solution. The solid remaining in the mixture was removed by filtration, and the ether layer was combined with chloroform extracts of the aqueous layer, dried over magnesium sulphate and evaporated to a residue. This residue and that from chloroform washings of the solid remaining after the Grignard reaction was crystallised from ethanol to give the title compound (0.56g.), m.p. 131°-3°C.

Workup

  1. customwas removed by filtration
  2. dry with materialdried over magnesium sulphate
  3. customevaporated to a residue
  4. customafter the Grignard reaction
  5. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-7720827c8b3e4075b67f331ad12e88c9
Source dataset
uspto-grants-1976_07
Patent number
US03969528

Reaction notes

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