Benzenemethanamine, 3,4-dichloro- → HCID 59392885, compound

HRID 222634Notes

Reaction equation

HRID 222634 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[C:25](=[O:46])[N:26]2[C:34](=[N:35][C:36]=1[C:37](O)=[O:38])[C:33]1[C:28](=[CH:29][CH:30]=[CH:31][C:32]=1[N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)[O:27]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[Cl:56])[CH2:51][NH2:52].ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[Cl:56])[CH2:51][NH:52][C:37]([C:36]1[N:35]=[C:34]2[N:26]([O:27][C:28]3[C:33]2=[C:32]([N:40]2[CH2:41][CH2:42][O:43][CH2:44][CH2:45]2)[CH:31]=[CH:30][CH:29]=3)[C:25](=[O:46])[C:24]=1[O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:38]

Participants

6

Reactant 4

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 58100961HCID 58100961, compound

Product 1

HCID 59392885HCID 59392885, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N′-Dicyclohexylcarbodiimide (110 mg, 0.522 mmol) was added to a stirred solution of the product from Example 19.6 (200 mg, 0.475 mmol) in dichloromethane (100 mL), After 30 min, N,N-dimethylaminopyridine (6 mg, 0.05 mmol), 3,4-dichlorobenzylamine (92 mg, 0.52 mmol) and 1-hyroxybenzotriazole (70 mg, 0.52 mmol) were added successively. The mixture was stirred at room temperature overnight and aqueous work-up and extraction afforded the crude product was further purified by column chromatography (hexane/ethyl acetate 4:1) as eluent to afford the desired product (120 mg, 44%) as a yellow solid.

Workup

  1. extractionaqueous work-up and extraction
  2. customafforded the crude product
  3. customwas further purified by column chromatography (hexane/ethyl acetate 4:1) as eluent

Sources & evidence

ORD record
ord-820bfd16a99f427b9803874abbcbc2fc
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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