Benzene → HCID 12832415, compound

HRID 1105541Notes

Reaction equation

HRID 1105541 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:32](=[CH:33][CH:34]=1)[C:16]1=[C:17](C3CCCCN3C(=O)C)[C:18](=[O:22])[NH:19][CH2:20][CH2:21][CH:15]1[CH2:14][CH2:13]2.O.[OH-].[Na+].[CH:38]1C=CC=CC=1>O1CCCC1>[N:3]1([CH2:6][CH2:7][C:17]2[C:18](=[O:22])[NH:19][CH2:20][CH2:21][CH:15]3[CH2:14][CH2:13][C:12]4[C:32](=[CH:33][CH:34]=[C:10]([O:9][CH3:8])[CH:11]=4)[C:16]=23)[CH2:4][CH2:5][CH2:38][CH2:2][CH2:1]1

Participants

7

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20555596HCID 20555596, compound

Product 1

HCID 12832415HCID 12832415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25.7 ml of 1.1 M alane-triethylamine in benzene are added dropwise to the suspension of 7.7 g of [9-methoxy-2-oxo-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-1yl]-acetyl-piperidine in 85 ml of anhydrous tetrahydrofuran at 0°. The mixture is stirred for 3 hours at 0° and at room temperature for one hour. It is cooled, 20 ml of water are added dropwise, followed by 20 ml of 3 N aqueous sodium hydroxide. The resulting mixture is extracted with 400 ml of diethyl ether, the extract dried, evaporated, the residue crystallized from petroleum ether and recrystallized from ethyl acetate-hexane to give the 1-(2-piperidinoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 125°-128°. Its hydrochloride melts (after drying at 100°/0.01 mmHg) at 223°-225°.

Workup

  1. temperatureIt is cooled
  2. extractionThe resulting mixture is extracted with 400 ml of diethyl ether
  3. customthe extract dried
  4. customevaporated
  5. customthe residue crystallized from petroleum ether
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dbd69da5db604883ada8a893b61e534b
Source dataset
uspto-grants-1982_01
Patent number
US04309345

Reaction notes

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