Triethylamine → HCID 18668142, compound

HRID 1416135Notes

Reaction equation

HRID 1416135 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.N[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.C([N:27](CC)CC)C>C(Cl)(Cl)Cl>[CH2:18]([N:15]1[CH2:16][CH2:17][CH:12]([C:9]2[CH:10]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=2[C:6]([NH2:27])=[O:7])[CH2:13][CH2:14]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 18668142HCID 18668142, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The 4-iodobenzoyl chloride was dissolved in chloroform (40 mL) and added to a flask containing 4-amino-1-benzyl-piperidine (2.29 g, 12.1 mmol) in chloroform (75 mL) and triethylamine (20 mL). The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The resulting slurry was washed with water (100 mL). The organics were dissolved in CHCl3 (100 mL), separated from the aqueous layer and dried over anhydrous Na2SO4. The solvent was removed to give a solid (yield, 86%), m.p. 206° C. m/e=420 (M+). 1H R (δ ppm): 1.47-1.60 (m, 2H, CH2); 1.97-2.11 (m, 2H, CH2); 2.15-2.19 (m, 2H, CH2); 2.81-2.85 (m, 2H, CH2); 3.49 (s, 2H, benzyl CH2); 3.91-3.97 (m, 1H, CH); 5.98-6.00 (d, 1H, NH); 7.22-7.30 (m, 5H arom); 7.43-7.45 (d, 2H, J=8 Hz, para substituted arom); 7.73-7.76 (d, 2 H, J=8 Hz, para substituted arom). 13C NMR (δ ppm): 32.23, 47.19, 52.25, 63.01, 127.14, 128.27, 128.49, 129.14, 134.18, 137.75, 138.14, 166.02)

Workup

  1. additionadded to a flask
  2. customthe volatiles were removed in vacuo
  3. washThe resulting slurry was washed with water (100 mL)
  4. dissolutionThe organics were dissolved in CHCl3 (100 mL)
  5. customseparated from the aqueous layer
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed
  8. customto give
  9. customa solid (yield, 86%), m.p. 206° C. m/e=420 (M+)

Sources & evidence

ORD record
ord-c90ad54129b14b98870156a176a5bb0c
Source dataset
uspto-grants-1999_06
Patent number
US05911970

Reaction notes

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