Sodium Hydroxide → HCID 131725884, compound

HRID 7407Notes

Reaction equation

HRID 7407 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]([C:15]3[N:16]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=[CH:18][N:19]=3)(O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-:28].[Cl-].[Cl-].[OH-].[Na+]>>[ClH:28].[ClH:28].[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]3([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[CH2:20][N:16]4[CH:17]=[CH:18][N:19]=[C:15]34)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) Chloride2×HCID 219901871-(Phenylmethyl)-4-[1-(phenylmethyl)-1h-imidazol-2-yl]-4-piperidinol

Product 1

HCID 131725884HCID 131725884, compoundYield 1.8%

Conditions

Temperature
120 °C

Procedure

1-(phenylmethyl)-4-[1-(phenylmethyl)-1H-imidazol-2-yl]-4-piperidinol (0.124 mol) and AlCl3 (0.31 mol) were stirred in a melt at 120° C. for 1 h. The mixture was cooled, AlCl3 (0.31 mol) was added and the mixture was stirred at 120° C. for 1 h. The mixture was poured into ice, alkalized with NaOH 50% and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered off and evaporated. The residue was purified by HPLC (eluent: CH2Cl2/(CH3OH/NH3) 99/1). The pure fractions were collected and evaporated. The residue was converted into the hydrochloric acid salt (1:2) in (C2H5)2O, yielding 0.91 g of 1′-(phenylmethyl)spiro[imidazo[1,2-b]isoquinoline-10[5H],4′-piperidine]dihydrochloride.dihydrate (2%) (interm. 3; mp. 161.2° C.).

Workup

  1. temperatureThe mixture was cooled
  2. additionThe mixture was poured into ice
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated
  7. customThe residue was purified by HPLC (eluent: CH2Cl2/(CH3OH/NH3) 99/1)
  8. customThe pure fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-36dcda66a7bc4f35af86da77d22e3518
Source dataset
uspto-grants-2006_08
Patent number
US07087595B2

Reaction notes

Loading…