Hydrochloric Acid → HCID 21193082, compound

HRID 1068186Notes

Reaction equation

HRID 1068186 reaction equation
C([Cl:4])(=O)C.Cl.C(OC([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:25][CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[O:21][C:20]2=[O:30])[CH2:15][CH2:14]1)=O)(C)(C)C>CO>[ClH:4].[CH:26]1[C:23]2[CH2:24][CH2:25][N:19]([CH:16]3[CH2:17][CH2:18][NH:13][CH2:14][CH2:15]3)[C:20](=[O:30])[O:21][C:22]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 21193013HCID 21193013, compound

Product 1

HCID 21193082HCID 21193082, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetyl chloride (0.2 mL, 2.8 mmol) was added to 2 mL of methanol and stirred for 10 min. This solution of HCl in MeOH was added to 58 mg of 1-t-butyloxycarbonyl-4-(8,9-dihydro-7H-5-oxa-7-aza-benzocyclohepten-6-one-7-yl)-piperidine (Step A) and stirred for 2 hr. The reaction was concentrated in vacuo, the residue was diluted with EtOAc and the solution was concentrated again in vacuo leaving 46 mg of the title compound which was sufficiently pure for use in the next step. 1H NMR (500 MHz, CDCl3): δ2.06 (m, 2H), 2.35 (m, 2H), 3.02 (m, 4H), 3.5-3.8 (m, 4H), 4.35 (br s, 1H), 7.1-7.3 (m, 4H), 9.6 (br, 2H).

Workup

  1. stirringstirred for 2 hr
  2. concentrationThe reaction was concentrated in vacuo
  3. additionthe residue was diluted with EtOAc
  4. concentrationthe solution was concentrated again in vacuo

Sources & evidence

ORD record
ord-dbc92b0d32f941298fe9d50575c9f1d3
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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