Triethylamine → HCID 86759684, compound

HRID 1816721Notes

Reaction equation

HRID 1816721 reaction equation
Cl.Cl.[CH3:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.O[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.O>[N:34]1([O:29][C:28](=[O:30])[C:27]2[CH:26]=[CH:25][C:24]([N:21]3[CH2:22][CH2:23][N:18]([C:15]4[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH3:3])=[CH:17][CH:16]=4)[CH2:19][CH2:20]3)=[CH:32][CH:31]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69677635HCID 69677635, compound

Product 1

HCID 86759684HCID 86759684, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-[4-(6-methoxyhexyloxy)phenyl]piperazin-1-yl]benzoic acid dihydrochloride (2.00 g) and 1-hydroxybenzotriazole (0.84 g) in methylene chloride (40 ml) was treated with triethylamine (1.44 ml) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, and the mixture was stirred for 24 hours at ambient temperature. The reaction mixture was added to water. The organic layer was taken, washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution successively, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. To the residue was added diisopropyl ether, and the resulting precipitate was filtered, washed with diisopropyl ether and dried under reduced pressure to give 4-[4-(4-(6-methoxyhexyloxy)phenyl]piperazin-1-yl]benzoic acid benzotriazol-1-yl ester (2.30 g) as a dark yellow solid.

Workup

  1. washwashed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution successively
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. additionTo the residue was added diisopropyl ether
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with diisopropyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-511d3c11627f4e15a2867aa76219cf09
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…