Toluene → HCID 86744655, compound

HRID 358776Notes

Reaction equation

HRID 358776 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[C:7]([N:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH2:15][CH2:16][C:17](OCC)=[O:18])[CH2:10]1)=O.C(N(CC)CC)C.C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>O>[ClH:1].[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:7][N:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:10]1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 86744656HCID 86744656, compound

Product 1

HCID 86744655HCID 86744655, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-(3,4,5-trimethoxybenzoyl)2-piperazine propionate hydrochloride obtained in Reference Example 31 (1.3 g), triethylamine (315 mg) and toluene (10 ml) is added dropwise, while stirring, at room temperature a 3.4M toluene solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (9 g). To the reaction mixture, after stirring for 3 hours, is added water, followed by extraction with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is led to its hydrochloride, which is recrystallized from ethanol to give 4-(3,4,5-trimethoxybenzyl)-2piperazine propanol dihydrochloride as colorless crystals (1 0 g) m.p. 212-215° C.

Workup

  1. additionis added dropwise
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-5a4cd516dc81456e8797fada9b897889
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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