Pyridine → HCID 86743854, compound

HRID 2073347Notes

Reaction equation

HRID 2073347 reaction equation
CS(NCCN[C@@:9]1(CCN)[CH2:18][C@@H:17]2[N:12]([CH2:13][CH2:14][C:15]3[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:16]=32)[CH2:11][CH2:10]1)(=O)=O.C(Cl)Cl.N1C=CC=[CH:33][CH:32]=1.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH:18]1[CH2:9][CH:10]=[CH:11][N:12]2[C:17]=1[C:16]1[O:23][C:21]3[CH:20]=[CH:19][CH:33]=[CH:32][C:22]=3[C:15]=1[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6371PhosgeneHCID 86743855HCID 86743855, compound

Product 1

HCID 86743854HCID 86743854, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.50 grams (11.35 mmol) of (2R,11bS) 2-(2-methanesulfonamidoethylamino)-2-(2-aminoethyl)-9-methoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine and 600 milliliters of methylene chloride containing 6.02 milliliters (25.01 mmol) of dry pyridine was cooled to 0° C. and 6.02 milliliters (11.91 mmol) of a 1.98M solution of phosgene in toluene was added dropwise over two hours. The mixture was stirred overnight at room temperature, washed with saturated aqueous NaHCO3 and brine, dried, filtered and concentraed in vacuo. The residue was chromatographed on 80 grams of silica gel using 1:4 methanolethyl acetate as eluant to obtain 1 gram of (2R,11bS) 9-methoxy-1,3,4,5',6,6',7,11b-octahydro-3'-(2-methanesulfonamidoethyl)-spiro-benzo[a]quinolizine-2,4'-(1'H-pyrimidin-2'-(3'H)-one as the free base. The HCl salt was prepared from 2-propanol and concentrated HCl. The HCl salt has a melting point 170°-174° C. with decomposition. The specific rotation for the HCl salt was -32.2°, c=0.012 g/ml, methanol.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. filtrationfiltered
  4. customThe residue was chromatographed on 80 grams of silica gel using 1:4 methanolethyl acetate as eluant

Sources & evidence

ORD record
ord-1388fe61ca5e498381982f4b0f8347ec
Source dataset
uspto-grants-1990_04
Patent number
US04916223

Reaction notes

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