Trimethylamine → HCID 14676164, compound

HRID 1638792Notes

Reaction equation

HRID 1638792 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[CH2:16][CH2:15]3)=[O:13])[CH2:8][CH2:9]2)=[CH:4][CH:3]=1.C(OCC)(=O)C.CN(C)C.[C:43](Cl)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(O)C>[C:43]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[CH2:16][CH2:15]3)=[O:13])[CH2:8][CH2:9]2)=[CH:4][CH:3]=1)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 14676162HCID 14676162, compound

Product 1

HCID 14676164HCID 14676164, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(7-hydroxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine (0.2 g), ethyl acetate (20 ml), trimethylamine (0.5 g) and benzoyl chloride (0.5 g) is left standing for 7 hours at room temperature. To the mixture is added ethanol (2 ml), and the mixture is left standing overnight. The solvent is distilled off under reduced pressure. To the residue is added ethyl acetate (50 ml), and insolubles are filtered off. The filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:acetone=1:1-1:2) and crystallized from ethyl ether to afford 1-(7-benzoyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine (0.15 g) as colorless prisms, m.p. 117°-119° C.

Workup

  1. waitis left
  2. waitthe mixture is left
  3. waitstanding overnight
  4. distillationThe solvent is distilled off under reduced pressure
  5. additionTo the residue is added ethyl acetate (50 ml), and insolubles
  6. filtrationare filtered off
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (hexane:acetone=1:1-1:2)
  9. customcrystallized from ethyl ether

Sources & evidence

ORD record
ord-50a44acd86844413ac852c11411feb0d
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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