4-Cyanobenzoic acid → HCID 18327620, compound

HRID 1250410Notes

Reaction equation

HRID 1250410 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)#[N:15].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:2]2[CH2:3][CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH2:1]2)=[O:21])=[CH:18][CH:17]=1)#[N:15]

Participants

6

Reactant 4

HCID 120874-Cyanobenzoic acidHCID 81531DiisopropylethylamineHCID 107838Tetrahydro-beta-carbolineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18327620HCID 18327620, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 175 mg of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, 5 ml of dimethylformamide, 0.2 g of 4-cyano-benzoic acid, 0.35 g of diphenylphosphoryl azide and 0.4 ml of diisopropylethylamine was stirred at room temperature over night. The solvent was removed under reduced pressure and the residue was partitioned between methylene chloride and 10% aqueous sodium carbonate solution. The organic phase was washed with 1 N hydrochloric acid, dried over magnesium sulfate and evaporated. Crystallization of the residue from methylene chloride/ether yielded 245 mg of 2-(4-cyano-benzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole with m.p. 228-232° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between methylene chloride and 10% aqueous sodium carbonate solution
  3. washThe organic phase was washed with 1 N hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customCrystallization of the residue from methylene chloride/ether

Sources & evidence

ORD record
ord-b29ba6496e654c38aa33db02285ecc4b
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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