tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[2-hydroxy-1-(4-methyl-piperazin-1-ylmethyl)ethyl]thiourea

HRID 47262

Reaction equation

HRID 47262 reaction equation
Cl.[NH2:2][CH:3]([CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)[CH2:4][OH:5].[C:14]([N:18]=[C:19]=[S:20])([CH3:17])([CH3:16])[CH3:15]>C(O)C.C(N(CC)CC)C.O.ClCCl>[C:14]([NH:18][C:19]([NH:2][CH:3]([CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]1)[CH2:4][OH:5])=[S:20])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 222939172-Amino-3-(4-methyl-piperazinyl)-1-propanol, hydrochloride

Product 1

HCID 9814494N-(tert-butyl)-N'-[2-hydroxy-1-(4-methyl-piperazin-1-ylmethyl)ethyl]thiourea

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1 g of 2-amino-3-(4-methyl-piperazin1-yl)-1-propanol hydrochloride in 20 mL of absolute ethanol and 1.43 mL of triethylamine, about 0.78 mL of tert-butylisothiocyanate are added. The reaction mixture is stirred under inert atmosphere at a temperature of about 20° C. for 42 hours then is heated at a temperature of about 50° C. for 1 hour 30 min. After cooling at a temperature of about 20° C., the reaction medium is evaporated under reduced pressure (2 kPa) at a temperature of about 30° C. The residue thus obtained is taken up in 10 mL of water and 40 mL of dichloromethane. The aqueous phase is extracted with 2 times 30 mL of dichloromethane. The organic phases are collected, washed with 15 mL of water, dried over magnesium sulfate, filtered, then concentrated under reduced pressure (2 kPa) at a temperature of about 20° C. About 0.42 g of N-(tert-butyl)-N′-[2-hydroxy-1-(4-methyl-piperazin-1-ylmethyl)ethyl]thiourea are obtained in the form of a white paste. [Infrared spectrum between lamella of KBr 3279; 3075; 2939; 2806; 1533; 1459; 1359; 1295; 1204; 1010 and 821 cm−1].

Workup

  1. temperaturethen is heated at a temperature of about 50° C. for 1 hour 30 min
  2. temperatureAfter cooling at a temperature of about 20° C.
  3. customthe reaction medium is evaporated under reduced pressure (2 kPa) at a temperature of about 30° C
  4. customThe residue thus obtained
  5. extractionThe aqueous phase is extracted with 2 times 30 mL of dichloromethane
  6. customThe organic phases are collected
  7. washwashed with 15 mL of water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure (2 kPa) at a temperature of about 20° C

Sources & evidence

ORD record
ord-5d1720e8385446ccb5a12f77754f97ce
Source dataset
uspto-grants-2004_03
Patent number
US06699867B2

Linked notes

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