4-Hydroxybenzaldehyde → HCID 18663243, compound

HRID 1956455Notes

Reaction equation

HRID 1956455 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>C(OCC)(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

Product 1

HCID 18663243HCID 18663243, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(N-Boc-piperidin-4-yl)propyl iodide 1-1 (5.0 g, 14.2 mmol) (preparation described in EP 478,328), 4-hydroxybenzaldehyde 1-2 (1.73 g, 14.2 mmol), Cs2CO3 (9.2 g, 28.4 mmol) and DMF (50 ml) was stirred at ambient temperature for 2.0 hours. The reaction mixture was diluted with ethyl acetate and then washed with H2O, sat. NaHCO3, 10% KHSO4, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 10% EtOAc/hexane) provided 1-3 as a white solid.

Workup

  1. washwashed with H2O, sat. NaHCO3, 10% KHSO4, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6768061557b7413a87d4bae93df62a2e
Source dataset
uspto-grants-1998_07
Patent number
US05780480

Reaction notes

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