Triethylamine → HCID 13520633, compound

HRID 1249150Notes

Reaction equation

HRID 1249150 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:11][CH2:10]1.C(N(CC)CC)C.[C:35](Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]([O:27][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 13520629HCID 13520629, compound

Product 1

HCID 13520633HCID 13520633, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7.27 g of 5-{2-[4-(2-methoxyphenyl)piperazinyl]ethyl}-8-hydroxy quinoline in 150 ml of anhydrous tetrahydrofuran in the presence of 3.1 ml of triethylamine and 5 ml of pivaloyl chloride is stirred for 48 hours at room temperature. After evaporation of the tetrahydrofuran, the residue is taken up in chloroform and washed with a 10% NaHCO3 solution. After evaporation of the chloroform, a crystalline residue is obtained which is recrystallised in 80 ml of isopropanol. Finally, 6.45 g of 5-{2-[4-(2-methoxyphenyl)piperazinyl]ethyl}-8-pivaloyloxy quinoline are obtained melting at 115° C.

Workup

  1. customAfter evaporation of the tetrahydrofuran
  2. washwashed with a 10% NaHCO3 solution
  3. customAfter evaporation of the chloroform
  4. customa crystalline residue is obtained which
  5. customis recrystallised in 80 ml of isopropanol

Sources & evidence

ORD record
ord-cf55db7f14324c68acefae253420492f
Source dataset
uspto-grants-1986_12
Patent number
US04629728

Reaction notes

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