4-Amino-2,2,6,6-tetramethylpiperidine → HCID 11825127, compound

HRID 377364Notes

Reaction equation

HRID 377364 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([OH:16])=O.[NH2:19][CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]1.O.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.[Cl-].[Na+].O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([NH:19][CH:20]1[CH2:21][C:22]([CH3:29])([CH3:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH2:25]1)=[O:16]

Participants

7

Reactant 4

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10955790HCID 10955790, compoundHCID 219174661-Hydroxy-7-azabenzotriazol hydrate

Product 1

HCID 11825127HCID 11825127, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid (122 mg, 0.5 mmol), 4-amino-2,2,6,6-tetramethylpiperidine (78 mg, 0.5 mmol), 1-hydroxy-7-azabenzotriazole hydrate (65 mg, 0.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (95 mg, 0.5 mmol) in DMF (2 ml) was stirred at RT for 6 hours. The solution was poured into brine (20 ml) and repeatedly extracted with EtOAc. The organic phase was washed with 5% aqueous CaCO3, dried (MgSO4) and concentrated to give a solid that was repeatedly washed with isopropyl ether. After drying pure title compound (45 mg, 0.12 mmol, yield 23.5%) was obtained as pale yellow crystals, mp.=250° dec.

Workup

  1. extractionrepeatedly extracted with EtOAc
  2. washThe organic phase was washed with 5% aqueous CaCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a solid
  6. washthat was repeatedly washed with isopropyl ether

Sources & evidence

ORD record
ord-78912a76eb564c70a274c5f436ba59d4
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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