Potassium Carbonate → Delequamine

HRID 476949Notes

Reaction equation

HRID 476949 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:21]=[CH:20][C:19]2[C@H:18]3[N:9]([CH2:10][C@@H:11]4[C@H:16]([CH2:17]3)[N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:14][CH2:13][CH2:12]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:2][O:3][C:4]1[CH:21]=[CH:20][C:19]2[C@H:18]3[N:9]([CH2:10][C@@H:11]4[C@H:16]([CH2:17]3)[N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:14][CH2:13][CH2:12]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 16889812-(Methanesulfonyl)-3-methoxy-5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquinolino[2,1-g][1,6]naphthyridine--hydrogen chloride (1/1)

Product 1

HCID 60713Delequamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(8aR,12aS,13aS)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine hydrochloride suspended in 50 ml of ethyl acetate is stirred with excess dilute aqueous potassium carbonate solution until the salt is completely dissolved. The organic layer is then separated, washed twice with water, dried over magnesium sulfate and evaporated to yield (8aR,12aS,13aS)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine, m.p. 165°-166° C.

Workup

  1. dissolutionis completely dissolved
  2. customThe organic layer is then separated
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4377700ea9a748978dc1b41f9f9c1eea
Source dataset
uspto-grants-1989_12
Patent number
US04886798

Reaction notes

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