Triethylamine hydrochloride → HCID 178420060, compound

HRID 2380330Notes

Reaction equation

HRID 2380330 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH:10]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:30]=[N+:31]=[N-:32].[Na+].Cl.C(N(CC)CC)C>CN1CCCC1=O>[C:1]1([C:7]2[N:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[NH:32][N:31]=[N:30][N:20]=3)[CH:10]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 18987239HCID 18987239, compound

Product 1

HCID 178420060HCID 178420060, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

By using a similar procedure to that described in example 9 but with 2.4 g 6-{[6-phenyl-4-(3,4-methylenedioxyphenyl)-2-pyridyl]oxy}hexanonitrile, 1.65 g of sodium azide, 1.3 g of triethylamine hydrochloride (in place of ammonium chloride) and 90 cc of N-methylpyrrolidone (in place of dimethylformamide) as the starting material (70 hours; 150° C.), and after purification by flash chromatography on silica gel (30-60 mm; eluent: ethyl acetate) and recrystallization from 18 cc of acetonitrile gives 5-{5-{[6-phenyl-4-(3,4-methylenedioxyphenyl)-2-pyridyl]oxy}pentyl }-1H-tetrazole (m.p.=150° C.)

Workup

  1. customafter purification by flash chromatography
  2. customon silica gel (30-60 mm; eluent: ethyl acetate) and recrystallization from 18 cc of acetonitrile

Sources & evidence

ORD record
ord-92f1db1eca914d37a58cb260142fbcd0
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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