Triethylamine → HCID 21073532, compound

HRID 1373572Notes

Reaction equation

HRID 1373572 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([O:12][CH:13]([CH3:18])[CH2:14][CH2:15][CH:16]=O)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Cl.[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:16][CH2:15][CH2:14][CH:13]([CH3:18])[O:12][C:8]2[N:9]=[C:10]3[C:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:11]3)=[CH:6][CH:7]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 21073378HCID 21073378, compound

Product 1

HCID 21073532HCID 21073532, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-pentanal (450 mg, crude) in DCE (10 mL) was added 2,3-dichlorophenyl-piperazine hydrochloride (495 mg, 1.85 mmol) followed by Et3N (0.55 mL, 3.96 mmol). The mixture was stirred for 10 min and then powdered NaBH(OAc)3 (534 mg, 2.52 mmol) was added. The reaction was stirred at room temperature for 2 h and then quenched with saturated NaHCO3. The mixture was extracted with EtOAc (2×). The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to give a foam. Purification by liquid chromatography (4% MeOH/CH2Cl2) gave the title compound as a white foam (507 mg, 1.09 mmol, 61%). MS: APCI: M+1: 463.1 (Exact Mass: 462.16). The enantiomers were separated by chiral HPLC (Chiralcel OD).

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customquenched with saturated NaHCO3
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. washThe organic layer was washed with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a foam
  8. customPurification by liquid chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fc6b999b543048eb98ef572430698d38
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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