N-Methylhomoveratrylamine → HCID 135493132, compound

HRID 1836118Notes

Reaction equation

HRID 1836118 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=1.[CH:15]1([C:20]2[C:24]3[N:25]=[C:26]([C:30]4[CH:31]=[C:32]([S:39](Cl)(=[O:41])=[O:40])[CH:33]=[CH:34][C:35]=4[O:36][CH2:37][CH3:38])[NH:27][C:28](=[O:29])[C:23]=3[O:22][N:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1>ClCCl>[CH:15]1([C:20]2[C:24]3[N:25]=[C:26]([C:30]4[CH:31]=[C:32]([S:39]([N:2]([CH2:3][CH2:4][C:5]5[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=5)[CH3:1])(=[O:40])=[O:41])[CH:33]=[CH:34][C:35]=4[O:36][CH2:37][CH3:38])[NH:27][C:28](=[O:29])[C:23]=3[O:22][N:21]=2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 77039N-MethylhomoveratrylamineHCID 135678135HCID 135678135, compound

Product 1

HCID 135493132HCID 135493132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

89.8 mg (0.46 mmol) of N-methylhomoveratrylamine are added to a solution of 65 mg (0.153 mmol) of the sulfonyl chloride from example IX in 5 ml of dichloromethane. The mixture is stirred overnight at room temperature before the crude product, after concentrating the mixture, is purified by means of preparative TLC chromatography using dichloromethane/methanol 95:5. The oily residue is crystallized with ether.

Workup

  1. concentrationafter concentrating the mixture
  2. customis purified by means of preparative TLC chromatography
  3. customThe oily residue is crystallized with ether

Sources & evidence

ORD record
ord-d826dfa5c7954add8d47b5143ba9175e
Source dataset
uspto-grants-2004_08
Patent number
US06777416B2

Reaction notes

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