Hydrochloric Acid → 4-methyl-N-(1,3-thiazol-2-ylmethyl)-1-piperazinamine

HRID 1366703Notes

Reaction equation

HRID 1366703 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([NH2:15])[CH2:11][CH2:10]1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.C([BH3-])#N.[Na+]>CO.O1CCOCC1>[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([NH:15][CH2:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:11][CH2:10]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 813491-Amino-4-methylpiperazineHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 669362614-methyl-N-(1,3-thiazol-2-ylmethyl)-1-piperazinamineYield 236.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available 1,3-thiazole-2-carbaldehyde (0.388 mL, 4.42 mmol) and commercially available 4-methyl-1-piperazinamine (0.532 mL, 4.42 mmol) were dissolved in MeOH (20 mL) and cooled to 0° C. Then methyl orange indicator and enough 4M HCl in dioxane was added to keep the reaction mixture acidic and a light pinkish color. Then sodium cyanoborohydride (0.555 g, 8.84 mmol) was added and the reaction was left to stir. The reaction mixture was evaporated to provide crude 4-methyl-N-(1,3-thiazol-2-ylmethyl)-1-piperazinamine as a beige-yellow solid (2.2168 g). LCMS: (M+H)+=213.0.

Workup

  1. waitthe reaction was left
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-d6f54bf0f10448dba75e30fb76506342
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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