Triethylamine → HCID 14751594, compound

HRID 330040Notes

Reaction equation

HRID 330040 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:13][NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N([CH2:34][CH3:35])CC)C.Cl[C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38]>ClCCl.CCOCC>[CH2:40]([O:39][C:37]([O:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:13][N:14]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][N:22]([C:37]([O:39][CH2:40][C:35]1[CH:34]=[CH:43][CH:42]=[CH:41][CH:46]=1)=[O:38])[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:38])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 253161,6-Naphthalenediol, 2,5-bis((cyclohexylamino)methyl)-

Product 1

HCID 14751594HCID 14751594, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,6-dihydroxy-2,5-bis-(cyclohexylaminomethyl)-naphthalene (3.8 g, 9.9 mmol) in dichloromethane (100 ml) were added, with cooling in an ice bath, triethylamine (6.9 ml, 50 mmol) and dropwise with stirring benzyl chloroformate (5.6 ml, 40 mmol). The reaction mixture was stirred at room temperature for 1 hour, diluted with ether, washed three times with water, dried (sodium sulfate) and evaporated to give the product as a thick syrup; yield 2.0 g.

Workup

  1. temperaturewith cooling in an ice bath
  2. washwashed three times with water
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-a7c72ece8bdd4fb6adfcf04dcad86cd2
Source dataset
uspto-grants-1990_01
Patent number
US04894392

Reaction notes

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