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4-Amino-1,2,2,6,6-pentamethylpiperidine → (2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-N[(1,2,2,6,6-pentamethyl)-piperidin-4-yl]-2,4-pentadienamide

HRID 377368
Notes
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Reaction equation

HRID 377368 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])[N:23]([CH3:28])[C:22]([CH3:30])([CH3:29])[CH2:21]1.O.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[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])([CH3:30])[N:23]([CH3:28])[C:24]([CH3:27])([CH3:26])[CH2:25]1)=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10955790(2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acidHCID 219174661-Hydroxy-7-azabenzotriazol hydrate

Product 1

HCID 18397576(2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-N[(1,2,2,6,6-pentamethyl)-piperidin-4-yl]-2,4-pentadienamide
Yield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid (122 mg, 0.5 mmol), 4-amino-1,2,2,6,6-pentamethylpiperidine (85 mg, 0.5 mmol), 1-hydroxy-7-azabenzotriazole hydrate (65 mg, 0.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (95 mg, 0.5 mmol) in DMF (2 ml) was stirred at RT overnight. After the same work-up described in example 3 the residue was triturated with isopropyl ether to produce a solid that was recovered and dried to give pure title compound (85 mg, 0.214 mmol, yield 42.8%) as yellow crystals, m.p.=152°.

Workup

  1. customwas triturated with isopropyl ether
  2. customto produce a solid
  3. customthat was recovered
  4. customdried

Sources & evidence

ORD record
ord-68d9ef7d8f504893b8a92ef1aa2a0dba
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06025390

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes