Triethylamine → 1-{1-[4-(3,4-Dichloro-benzoyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea

HRID 369924Notes

Reaction equation

HRID 369924 reaction equation
[NH2:1][CH:2]([CH:20]([CH3:22])[CH3:21])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[O:11])[CH2:6][CH2:5]1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[C:27](OC)[C:26]=1[O:36][CH3:37].C(N(CC)CC)C.[N-]=[C:46]=[O:47]>ClCCl>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[C:10]([CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([NH:1][C:32]([NH:31][C:28]2[CH:27]=[C:26]([O:36][CH3:37])[C:25]([O:24][CH3:23])=[C:30]([O:47][CH3:46])[CH:29]=2)=[O:33])[CH:20]([CH3:22])[CH3:21])[CH2:5][CH2:6]1)=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 105034IsocyanateHCID 11484673[1-(2-Amino-3-methylbutyl)piperidin-4-yl]-(3,4-dichlorophenyl)methanoneHCID 220281171-Isocyanato-2,3,4-trimethoxybenzene

Product 1

HCID 98290551-{1-[4-(3,4-Dichloro-benzoyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1-(2-amino-3-methylbutyl)piperidin-4-yl]-(3,4-dichlorophenyl)methanone (30 mg) in dichloromethane (3 mL) was treated with trimethoxyphenyl-isocyanate (30 mg) and triethylamine (1 mL, 0.3 M in dichloromethane) was added and the reaction mixture was stirred at ambient temperature overnight. A polystyrene trisamine resin (approx. 0.5 g, 3.5 mmol/g) was added to capture excess isocyanate, and stirring was continued for an additional 2 h. The resin was filtered and the filtrate was concentrated. Purification by column chromatography gave 1-{1-[4-(3,4-dichloro-benzoyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea (27.5 mg).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for an additional 2 h
  4. filtrationThe resin was filtered
  5. concentrationthe filtrate was concentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-054be61bc7dd420694cf4fe3426a5a8d
Source dataset
uspto-grants-2000_10
Patent number
US06140344

Reaction notes

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