Benzoyl chloride → HCID 4779138, compound

HRID 2381563Notes

Reaction equation

HRID 2381563 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH:1]1([CH2:7][NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 76688Cyclohexanemethylamine

Product 1

HCID 4779138HCID 4779138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexylmethylamine (4.37 mL, 33.6 mmol) was added to a solution of benzoyl chloride (2.47 mL, 21 mmol) in THF (20 mL) at 0° C., and stirring continued 16 h. The mixture was filtered, diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4), and concentrated in vacuo. The product crystallised (2.1 g, 45%) 1H-NMR (300 MHz, CDCl3) δH 7.76 (1H, m, Ar); 7.29 (8H, m, Ar); 1.04 (2H, m, CH2); 1.14 (2H, m, CH2); 1.61 (7H, m, 3×CH2); 3.23 (2H, t, J=6.78 Hz, N—CH2); 6.15 (1H, s, NH); 7.37 (3H, m, ArH), 7.70 (2H, m, ArH); LCMS (ESI+) 218 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with water (10 mL)
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe product crystallised (2.1 g, 45%) 1H-NMR (300 MHz, CDCl3) δH 7.76 (1H, m, Ar); 7.29 (8H, m, Ar); 1.04 (2H, m, CH2); 1.14 (2H, m, CH2); 1.61 (7H, m, 3×CH2); 3.23 (2H, t, J=6.78 Hz, N—CH2); 6.15 (1H, s, NH); 7.37 (3H, m, ArH), 7.70 (2H, m, ArH)

Sources & evidence

ORD record
ord-c1305972ecd64d15b07d9273914de0f1
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

Loading…