Hydrochloric Acid → HCID 18652824, compound

HRID 484009Notes

Reaction equation

HRID 484009 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:15][O:16][C:17]1[CH:34]=[CH:33][C:32]2[C@H:31]3[N:22]([CH2:23][C@@H:24]4[C@H:29]([CH2:30]3)[N:28]([S:35]([CH2:38][CH2:39][CH2:40]Cl)(=[O:37])=[O:36])[CH2:27][CH2:26][CH2:25]4)[CH2:21][CH2:20][C:19]=2[CH:18]=1.C(N(CC)CC)C.Cl>CN(C=O)C>[CH3:15][O:16][C:17]1[CH:34]=[CH:33][C:32]2[C@H:31]3[N:22]([CH2:23][C@@H:24]4[C@H:29]([CH2:30]3)[N:28]([S:35]([CH2:38][CH2:39][CH2:40][N:12]3[CH2:13][CH2:14][N:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])[CH2:10][CH2:11]3)(=[O:37])=[O:36])[CH2:27][CH2:26][CH2:25]4)[CH2:21][CH2:20][C:19]=2[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 57275675HCID 57275675, compound

Product 1

HCID 18652824HCID 18652824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.8 g of 4-(2-methoxyphenyl)piperazine, 1.8 g of (8aR,12aS,13aS)-3-methoxy-12-(3-chloropropane-sulfonyl)-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and 1 ml of triethylamine in 10 ml of DMF was stirred at 90° C. for 16 hours. The temperature was then raised to 120° C. for 8 hours and stirring continued. After cooling, the solution was acidified with 2N hydrochloric acid and then washed with ethyl acetate, the aqueous portion basified with aqueous ammonium hydroxide and extracted further with diethylether. The solvent was then dried over sodium sulfate and evaporated under reduced pressure. The residue was flash chromatographed on silica gel, eluting with ethyl acetate, to give (8aR,12aS,13aS)-3-methoxy-12-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propanesulfonyl}-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine, a compound of formula (I).

Workup

  1. temperatureThe temperature was then raised to 120° C. for 8 hours
  2. stirringstirring
  3. temperatureAfter cooling
  4. washwashed with ethyl acetate
  5. extractionextracted further with diethylether
  6. dry with materialThe solvent was then dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customchromatographed on silica gel
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-56910d82dfef49609d954fb5e5b1decb
Source dataset
uspto-grants-1993_07
Patent number
US05229387

Reaction notes

Loading…