Ammonium Chloride → HCID 67536962, compound

HRID 2383023Notes

Reaction equation

HRID 2383023 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1>[CH2:9]([N:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67537534HCID 67537534, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 67536962HCID 67536962, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an ice bath under argon flow, a solution of 1.07 M phenylmagnesium bromide in THF (33.2 mL) was added dropwise to a solution of 2-benzyl-1-phenyl-3,4-dihydroisoquinoline hydrobromate (8.95 g) in THF (80 mL) over 1 hour. The mixture was stirred at room temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the mixture which was then extracted with EtOAc. The extract was washed with water and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-benzyl-1,1-diphenyl-1,2,3,4-tetrahydroisoquinoline (1.81 g).

Workup

  1. extractionwas then extracted with EtOAc
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-4ee3ac662b1946cf8458beeb954ea712
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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