Dimethylformamide → HCID 22502878, compound

HRID 1007030Notes

Reaction equation

HRID 1007030 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[N:11][C:10]=2Br)[CH2:5][CH2:4]1)[CH3:2].C([Li])(C)(C)C.CN(C)[CH:27]=[O:28].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[N:11][C:10]=2[CH2:27][OH:28])[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22502986HCID 22502986, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 22502878HCID 22502878, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-ethylpiperidin-1-yl)-3-bromoisoquinoline (1.03 g) in tetrahydrofuran (20 ml) was cooled to −78° C., followed by the dropwise addition of 1.7M tert-butyllithium (3 ml). Fifteen minutes later, N,N-dimethylformamide (0.5 ml) was added thereto and the temperature of the reaction solution was raised to room temperature. To the reaction solution was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate, followed by washing with water and brine, drying and evaporating. The resulting residue was dissolved in methanol (15 ml), and reacted with sodium borohydride (0.4 g). The solvent was removed, the resulting residue was extracted with ethyl acetate extraction, followed by washing with water and brine, drying and evaporating. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 4-(4-ethylpiperidin-1-yl)-3-hydroxymethylisoquinoline (0.46 g, 52.7%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing with water and brine
  3. customdrying
  4. customevaporating
  5. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  6. customreacted with sodium borohydride (0.4 g)
  7. customThe solvent was removed
  8. extractionthe resulting residue was extracted with ethyl acetate extraction
  9. washby washing with water and brine
  10. customdrying
  11. customevaporating
  12. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-0b96f11a52e94f01ac866dfc4fe05cbd
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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