1-Naphthylamine → HCID 86753895, compound

HRID 1418529Notes

Reaction equation

HRID 1418529 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:23]1([CH2:36][O:37][C:38]([NH:40][C@H:41]([C:54](O)=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:39])[C:35]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1.[NH2:57][C:58]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH:61]=[CH:60][CH:59]=1>O.C(OCC)(=O)C>[C:58]1([NH:57][C:54](=[O:55])[C@H:41]([CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])[NH:40][C:38]([O:37][CH2:36][C:23]2[C:35]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]=3[CH:26]=[CH:25][CH:24]=2)=[O:39])[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH:61]=[CH:60][CH:59]=1

Participants

7

Reactant 4

HCID 86401-NaphthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86753896HCID 86753896, compound

Product 1

HCID 86753895HCID 86753895, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under cooling with ice water, 2.97 g (22 mmol) of 1-hydroxybenzotriazole and 4.60 g (24 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to an ethyl acetate solution (50 ml) of 9.37 g (20.0 mmol) of Nα-fluorenylmethyloxycarbonyl-Nε-t-butoxycarbonyl-L-lysine and 2.86 g (20.0 mmol) of 1-aminonaphthalene. The mixture was stirred overnight as it was. Water was added to the reaction mixture, and a solid deposited was collected by filtration, washed with ethyl acetate and dried, thereby obtaining 7.95 g of the title compound.

Workup

  1. filtrationa solid deposited was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-8ed8f818b33d4003892421092899d6ee
Source dataset
uspto-grants-1999_03
Patent number
US05883121

Reaction notes

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