Hydrochloric Acid → HCID 19769386, compound

HRID 1590046Notes

Reaction equation

HRID 1590046 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23](=[O:24])[C:22]3[CH:25]=[CH:26][C:27]([N+:28]([O-])=O)=[C:20]4[C:21]=3[C:16](=[CH:17][CH:18]=[CH:19]4)[C:15]2=[O:31])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+].C(Cl)Cl>C(O)(=O)C>[NH2:28][C:27]1[CH:26]=[CH:25][C:22]2[C:23](=[O:24])[N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:9][CH2:10]3)[C:15](=[O:31])[C:16]3[C:21]=2[C:20]=1[CH:19]=[CH:18][CH:17]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 19769350HCID 19769350, compound

Product 1

HCID 19769386HCID 19769386, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of stannous chloride (5.0 g; 22.2 mmol) and 2-(1-benzylpiperidin-4-yl)-2,3-dihydro-6-nitro-1H-benz[de]isoquinoline-1,3-dione (1.9 g; 4.75 mmol), prepared as in Example 3, in glacial acetic acid (5 mL) was added 10% hydrochloric acid (7 mL). The reaction mixture was stirred for 2 hours and then a mixture of 10% sodium hydroxide and methylene chloride was added. The aqueous layer was extracted three additional times with methylene chloride and then the combined extracts were dried over potassium carbonate. Filtration and concentration of the methylene chloride extracts gave 6-amino-2-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione (1.5 g; 3.90 mmol), m.p. 226°-228° C. Anal.: Calcd. for C21H21N3O3Cl2 . 0.333 H2O: C, 57.30; H, 4.96; N, 9.54. Found: C, 57.39; H, 5.06; N, 9.52.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted three additional times with methylene chloride
  3. dry with materialthe combined extracts were dried over potassium carbonate
  4. filtrationFiltration and concentration of the methylene chloride

Sources & evidence

ORD record
ord-fa47173c57b44f3dbba285895d3f4ab6
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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