Diethyl Ether → 7-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine dihydrochloride

HRID 412514Notes

Reaction equation

HRID 412514 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][NH:21][CH2:22]4)=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[ClH:34].[N:35]1([C:40](N)=[NH:41])C=CC=N1.C(OCC)C>CN(C)C=O>[ClH:34].[ClH:34].[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][N:21]([C:40]([NH2:41])=[NH:35])[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 113247627-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 114419847-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine dihydrochlorideYield 127.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline (50 mg) in dimethylformamide (0.5 ml) were added diisopropylethylamine (0.027 ml) and 1H-pyrazole-1-carboxamidine hydrochloride (23 mg), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, diethyl ether was added and insoluble material was collected by filtration. The obtained solid was washed with diethyl ether. A part (45 mg) of the obtained solid was treated with hydrogen chloride-methanol and dried under reduced pressure to give the title compound (44 mg).

Workup

  1. additionwas added
  2. filtrationinsoluble material was collected by filtration
  3. washThe obtained solid was washed with diethyl ether
  4. additionA part (45 mg) of the obtained solid was treated with hydrogen chloride-methanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f77bcf09cffb48e9b166fa6f843ca56a
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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