Benzoyl chloride → HCID 14277502, compound

HRID 1461749Notes

Reaction equation

HRID 1461749 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C@H:11]1[CH2:25][C@H:24]2[C@@H:14]([CH2:15][C:16]3[C:26]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=4)[NH:18][CH:17]=3)[N:13]([CH2:27][CH2:28][CH3:29])[CH2:12]1>C(Cl)Cl.C(N(CC)CC)C>[C:1]([NH:10][C@H:11]1[CH2:25][C@H:24]2[C@@H:14]([CH2:15][C:16]3[C:26]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=4)[NH:18][CH:17]=3)[N:13]([CH2:27][CH2:28][CH3:29])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 134688038alpha-Amino-6-n-propylergoline

Product 1

HCID 14277502HCID 14277502, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

1.4 ml benzoylchloride in 5 ml CH2Cl2 are added drop-wise with stirring at 5°-10° C. to a suspension of 3.0 g 8α-amino-6-n-propylergoline in 100 ml CH2Cl2 and 2.0 ml triethylamine. The obtained reaction mixture is stirred for 15 to 20 hours at 20° C. and then washed thoroughly 2× with 25 ml 2N NaOH and H2O. The organic phase is dried over MgSO4, filtered and evaporated. The residue (pale brown foam) is dissolved in ethanol, and crystallised as the hydrobromide by addition of equivalent amounts of HBr in acetic acid. M.P. on recrystallisation from C2H5OH/H2O (80:2)=290° with decomposition.

Workup

  1. customThe obtained reaction mixture
  2. washwashed thoroughly 2× with 25 ml 2N NaOH and H2O
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue (pale brown foam) is dissolved in ethanol
  7. customcrystallised as the hydrobromide by addition of equivalent amounts of HBr in acetic acid
  8. customM.P. on recrystallisation from C2H5OH/H2O (80:2)=290° with decomposition

Sources & evidence

ORD record
ord-9012bb01317a4757b0e5e9c0ea6ce225
Source dataset
uspto-grants-1991_12
Patent number
US05077298

Reaction notes

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