Methyl 4-bromoacetylphenoxyacetate → Methyl 4-[2-[4-(5,6,7,8-tetrahydro-4-quinolinyl)piperazin-1-yl]-acetyl]phenoxyacetate

HRID 864786

Reaction equation

HRID 864786 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:17]1([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.N1(C2C3CCCCC=3N=CC=2)CCNCC1>C(#N)C>[N:26]1[C:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C:32]=2[C:23]([N:17]2[CH2:18][CH2:19][N:20]([CH2:2][C:3]([C:5]3[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:21][CH2:22]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 243438Methyl 4-bromoacetylphenoxyacetateHCID 15343864-Piperazin-1-yl-quinolineHCID 189184264-(Piperazin-1-yl)-5,6,7,8-tetrahydroquinoline

Product 1

HCID 18924099Methyl 4-[2-[4-(5,6,7,8-tetrahydro-4-quinolinyl)piperazin-1-yl]-acetyl]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Example 1, methyl 4-bromoacetylphenoxyacetate (1.23 g), a 1:1 mixture containing 4-(1-piperazinyl)quinoline and 4-(1-piperazinyl)-5,6,7,8-tetrahydroquinoline (1.84 g) and acetonitrile (56 ml) yielded, after stirring at room temperature overnight, filtration and evaporation of the filtrate, an orange/brown oily residue which was purified by flash chromatography, first on neutral alumina by elution with 5% v/v methanol/dichloromethane, then on silica by elution with methanol/dichloromethane (0.5% v/v to 5% v/v), and finally by crystallisation of the lower Rf material from methanol/water, to yield the title compound (298 mg) as a cream solid: NMR (CDCl3) δ1.76 (2H, m), 1.89 (2H, m), 2.64 (2H, m), 2.76 (4H, m), 2.95 (2H, m), 3.07 (4H, m), 3.80 (2H, s), 3.81 (3H, s), 4.71 (2H, s), 6.68 (1H, d), 6.95 (2H, d), 8.03 (2H, d) 8.28 (1H, d); m/Z 424 (M+H)+ ; calculated for C24H29N3O4. 1.0 H2O: C, 65.3%; H, 7.08%; N, 9.52%; found: C, 65.6%; H, 6.7%; N, 9.3%.

Workup

  1. customyielded
  2. filtrationfiltration and evaporation of the filtrate
  3. customan orange/brown oily residue which was purified by flash chromatography, first on neutral alumina by elution with 5% v/v methanol/dichloromethane
  4. washon silica by elution with methanol/dichloromethane (0.5% v/v to 5% v/v), and
  5. customfinally by crystallisation of the lower Rf material from methanol/water

Sources & evidence

ORD record
ord-434a6d501beb4a898364ec078ee92640
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Linked notes

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