Hydrochloric Acid → 12-(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)

HRID 476948Notes

Reaction equation

HRID 476948 reaction equation
[ClH:1].[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(OCC)C>CO>[ClH:1].[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 60713Delequamine

Product 1

HCID 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)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Excess 3% hydrogen chloride in methanol is added to a solution of (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 in 20 ml methanol. Diethyl ether is added until precipitation is complete. The product is filtered, washed with ether, air dried and recrystallized from methanol/acetone 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 hydrochloride.

Workup

  1. filtrationThe product is filtered
  2. washwashed with ether, air
  3. customdried
  4. customrecrystallized from methanol/acetone

Sources & evidence

ORD record
ord-cb931d2ce2344c4a834ca3fde79ed764
Source dataset
uspto-grants-1989_12
Patent number
US04886798

Reaction notes

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