HCID 12798064, compound → HCID 12798067, compound

HRID 1659524Notes

Reaction equation

HRID 1659524 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([CH:5]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH:6]1[C:7]1[N:8]([CH3:20])[C:9]3[C:14]([C:15]=12)=[CH:13][CH:12]=[CH:11][CH:10]=3)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:21][N:2]([CH2:3][CH:5]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH:6]1[C:7]1[N:8]([CH3:20])[C:9]3[C:14]([C:15]=12)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:1]

Participants

4

Reactant 2

HCID 12798064HCID 12798064, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12798067HCID 12798067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,2,3,4-tetrahydro-N,N,9-trimethyl-1,4-ethanocarbazole-2-carboxamide (0.40 g, 0.0015 mole, described in Example 4) in anhydrous tetrahydrofuran (10 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (0.050 g, 0.0015 mole) in anhydrous tetrahydrofuran (10 ml) under nitrogen at 0° C. Stirring was continued for 3 hr at room temperature and at reflux for one hr. The excess hydride was destroyed by dropwise addition of water to the cooled mixture (0° C.). Saturated sodium chloride solution was added and the compound was extracted with diethyl ether. The ether solution was extracted with dilute hydrochloric acid and the aqueous extract was basified with 10% aqueous sodium hydroxide. The alkaline solution was extracted with diethyl ether. The organic solution was dried and evaporated to dryness to afford a colorless oil of the title compound. Addition of a solution of hydrogen chloride in diethyl ether to a solution of the compound in diethyl ether gave the hydrochloride salt (0.35 g) of the title compound: mp 239° -241° C.; NMR (CDCl3) δ 0.8-2.3 (m, 7H), 2.4-2.75 (m, 8H), 3.5-4.0 (m, 2H), 3.90 (s, 3H) and 6.9-7.7 (m, 4H); and Anal. Calcd for C18H24N2.HCl: C, 70.91% H, 8.27% N, 9.19% and Found: C, 70.38% H, 8.28% N, 9.26%.

Workup

  1. temperatureat reflux for one hr
  2. customThe excess hydride was destroyed by dropwise addition of water to the cooled mixture (0° C.)
  3. additionSaturated sodium chloride solution was added
  4. extractionthe compound was extracted with diethyl ether
  5. extractionThe ether solution was extracted with dilute hydrochloric acid
  6. extractionthe aqueous extract
  7. extractionThe alkaline solution was extracted with diethyl ether
  8. customThe organic solution was dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-c246e9f28a264140af7801cb7c60edbc
Source dataset
uspto-grants-1981_12
Patent number
US04304772

Reaction notes

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