1-Cyclopentylpiperazine → HCID 59730338, compound

HRID 130755

Reaction equation

HRID 130755 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=O.[CH:19]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[CH:19]1([N:24]2[CH2:25][CH2:26][N:27]([CH2:1][C:3]3[CH:18]=[CH:17][C:6]([O:7][C:8]4[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=4)=[CH:5][CH:4]=3)[CH2:28][CH2:29]2)[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 8064211-CyclopentylpiperazineHCID 4311764Sodium borohydrideHCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide2×

Product 1

HCID 59730338HCID 59730338, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 6-(4-formyl-phenoxy)-nicotinamide (compound of example 332, step 1) (0.303 g, 1.25 mmol) and 1-cyclopentyl piperazine (0.198 g, 1.28 mmol) in methanol (11 mL) and stir. After 15.5 h, add sodium borohydride (0.109 g, 2.88 mmol), and stir at ambient temperature. After 1 h, concentrate the reaction mixture and purify by silica gel chromatography (ethyl acetate→4:1 ethyl acetate:methanol) to provide 0.172 g (36%) of the title compound as an off white solid: high resolution mass spectrum (electrospray): m/z calc for C22H29N4O2 381.2291, found 381.2306; 1H NMR (DMSO-d6): 8.66 (d, 1H, J=2.4 Hz), 8.30 (dd, 1H, J=2.9, 8.8 Hz), 7.48-7.43 (m, 2H), 7.18-7.13 (m, 2H), 7.04 (d, 1H, J=7.8 Hz), 3.61 (s, 2H), 3.00-2.25 (m, 9H), 2.01-1.88 (m, 2H), 1.82-1.69 (m, 2H), 1.69-1.56 (m, 2H), 1.53-1.38 (m, 2H).

Workup

  1. waitAfter 1 h
  2. concentrationconcentrate the reaction mixture
  3. custompurify by silica gel chromatography (ethyl acetate→4:1 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-500fdcd8ff9848fe94c4841e5bd5c97a
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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