Piperonal → HCID 21104563, compound

HRID 1354235Notes

Reaction equation

HRID 1354235 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[NH2:12][CH2:13][CH:14]1[O:19][CH2:18][CH2:17][N:16]([CH2:20][CH:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)[OH:22])[CH2:15]1.[BH4-].[Na+]>C(Cl)Cl.CO>[O:11]1[C:3]2[CH:2]=[CH:1][C:6]([CH2:7][NH:12][CH2:13][CH:14]3[O:19][CH2:18][CH2:17][N:16]([CH2:20][CH:21]([C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=5)[N:26]=[CH:25][CH:24]=4)[OH:22])[CH2:15]3)=[CH:5][C:4]=2[O:9][CH2:10]1

Participants

6

Reactant 3

HCID 8438PiperonalHCID 4311764Sodium borohydrideHCID 21104562HCID 21104562, compound

Product 1

HCID 21104563HCID 21104563, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Activated 3A molecular sieve (3.485 g) and piperonal (0.172 g, 1.15 mmol) were added to a solution of 2-(2-aminomethyl-morpholin-4-yl)-1-(6-methoxy-quinolin-4-yl)-ethanol (0.365 g, 1.15 mmol) in DCM (10.5 ml) and methanol (3.5 ml). The mixture was stirred overnight at room temperature before sodium borohydride (0.112 g, 2.9 mmol) was added. The reaction mixture was stirred at room temperature for a further 2 hours, filtered over Hydromatrix (wetted with NaHCO3) and concentrated. The residue was purified by chromatography on silica gel (DCM:MeOH 9:1+1% NH4OH).

Workup

  1. additionwas added
  2. filtrationfiltered over Hydromatrix (wetted with NaHCO3)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (DCM:MeOH 9:1+1% NH4OH)

Sources & evidence

ORD record
ord-c53ea5fe8691464e9dce280541e4521e
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

Loading…