Tetrahydrofuran → HCID 178505638, compound

HRID 414234Notes

Reaction equation

HRID 414234 reaction equation
C1COCC1.[Al+3].[Cl-].[Cl-].[Cl-].[N-:10]=[N+:11]=[N-:12].[Na+].[CH2:14]([N:21]1[CH2:26][CH2:25][C:24]([C:35]#[N:36])([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([N:21]1[CH2:22][CH2:23][C:24]([C:35]2[NH:36][N:12]=[N:11][N:10]=2)([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[CH2:25][CH2:26]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 14225434HCID 14225434, compound

Product 1

HCID 178505638HCID 178505638, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 ml of stirring dry THF in a 500 ml r.b. flask at 0° C. under N2, AlCl3 (23.0 g, 172 mmol) was added in small portions. Subsequently, NaN3 (47.4 g, 729 mmol) and 1-benzyl-4-cyano-4-(2-fluoroanilino)piperidine (21.8 g, 70 mmol) were added. The resulting mixture was refluxed for 20 hours. It was cooled to room temperature and poured onto stirring water (300 ml). The THF layer was separated and the aqueous layer was extracted with additional THF (3×500 ml). The combined THF layers were dried over MgSO4 and filtered. The filtrate was kept at 0° C. for 15 hours. After a filtration, the desired compound (17.1 g, 49 mmol) as white powder was obtained: m.p. 195°-198° C.; IR (nujol) 3360 cm-1 ; NMR (270 MHz, DMSO-d6) δ 2.29, 2.46 and 2.67 (3m, 8H, piperidine CH2 's), 3.53 (s, 2H, benzyl CH2), 6.12, 6.61, 6.72 and 6.98 (4m, 4H, anilinophenyl) H's), 7.2-7.4 (m, 5H, benzylphenyl H's). Anal. Calcd. for C19H21FN6 : C, 64.75; H, 6.01; N, 23.85. Found: C, 64.52; H, 5.94; N, 23.56. ##STR23##

Workup

  1. temperatureThe resulting mixture was refluxed for 20 hours
  2. additionpoured
  3. customThe THF layer was separated
  4. extractionthe aqueous layer was extracted with additional THF (3×500 ml)
  5. dry with materialThe combined THF layers were dried over MgSO4
  6. filtrationfiltered
  7. filtrationAfter a filtration

Sources & evidence

ORD record
ord-c7952db22c0c400eae297f26884283aa
Source dataset
uspto-grants-1988_12
Patent number
US04791120

Reaction notes

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