Triethylamine → 1-[4-[4-(4-Hexyloxyphenyl)piperazin-1-yl]benzoyloxy]benzotriazole

HRID 351553Notes

Reaction equation

HRID 351553 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.Cl.[CH2:12]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O.ClCCl>[CH2:12]([O:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:39]=[CH:38][C:34]([C:35]([O:1][N:2]4[C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[N:4]=[N:3]4)=[O:36])=[CH:33][CH:32]=3)[CH2:29][CH2:30]2)=[CH:23][CH:24]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 698180334-[4-(4-Hexyloxyphenyl)piperazin-1-yl]benzoic acid hydrochloride

Product 1

HCID 227132451-[4-[4-(4-Hexyloxyphenyl)piperazin-1-yl]benzoyloxy]benzotriazoleYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-hydroxybenzotriazole (5.35 g) and 4-[4-(4-hexyloxyphenyl)piperazin-1-yl]benzoic acid hydrochloride (15 g) in the mixture of triethylamine (9.64 ml) and dichloromethane (450 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl) carbodiimide hydrochloride (WSCD.HCl) (12.6 g) and stirred for 4 hours at ambient temperature. The reaction mixture was added to water. The organic layer was taken and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-[4-[4-(4-hexyloxyphenyl)piperazin-1-yl]benzoyloxy]benzotriazole (16.78 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationMagnesium sulfate was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1394ded476814c2bb9f1ccf9d009a025
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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