Hydrochloric Acid → 2-((1-Benzyl-piperidin-4-ylamino)-methyl)-phenyl-ammonium dihydrochloride

HRID 239109Notes

Reaction equation

HRID 239109 reaction equation
O.O.[Sn](Cl)[Cl:4].[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-])=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C=O)C.[ClH:35]>C(O)C>[ClH:4].[ClH:35].[CH2:6]([N:13]1[CH2:14][CH2:15][CH:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH3+:27])[CH2:17][CH2:18]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 61436Stannous chloride dihydrateHCID 48487621-benzyl-N-[(2-nitrophenyl)methyl]piperidin-4-amine

Product 1

HCID 866864862-((1-Benzyl-piperidin-4-ylamino)-methyl)-phenyl-ammonium dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1 g tin (II) chloride-dihydrate was added to 290 mg (1-benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine in 18 mL ethanol. The reaction was refluxed for 15 min. DMF was added until the reaction was diluted. Then, 5 mL 10 M HCl in ethanol was added, the solvent was removed, 8 mL acetone was added and the mixture was stirred at RT. The precipitate was filtered to give 550 mg of the desired product. Rf: 0.35 (dichlormethane 9: methanol 1: ammonia 0.1), (M+H)+: 296

Workup

  1. temperatureThe reaction was refluxed for 15 min
  2. additionwas diluted
  3. customthe solvent was removed
  4. addition8 mL acetone was added
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-519a4f876a9b40c0a4e4884e2cf34328
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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