Hydrochloric Acid → 4-(4-Methyl-piperazin-1-ylmethyl)-4,5-dihydro-thiazol-2-ylamine, trihydrochloride

HRID 1765450Notes

Reaction equation

HRID 1765450 reaction equation
C([NH:5][C:6]([NH:8][CH:9]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:20]>>[ClH:20].[ClH:20].[ClH:20].[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 9814494N-(tert-butyl)-N'-[2-hydroxy-1-(4-methyl-piperazin-1-ylmethyl)ethyl]thiourea

Product 1

HCID 222939164-(4-Methyl-piperazin-1-ylmethyl)-4,5-dihydro-thiazol-2-ylamine, trihydrochloride

Conditions

Temperature
100 °C

Procedure

A suspension of 0.42 g de N-(tert-butyl)-N′-[2-hydroxy-1-(4-methyl-piperazin-1-ylmethyl)ethyl]-thiourea in 3.9 mL of an aqueous 6N hydrochloric acid is heated at a temperature of about 100° C. for 5 hours. After cooling, the reaction medium is concentrated under reduced pressure (2 kPa) at a temperature of about 55° C. The residue obtained is dried in an oven under vacuum (2 kPa) for 4 hours. About 0.47 g of 4-(4-methyl-piperazin-1-ylmethyl)-4,5-dihydro-thiazol-2-ylamine, trihydrochloride are obtained in the form of a very hygroscopic off-white paste. [1H NMR spectrum (300 MHz, (CD3)2SO d6 with addition of a few drops of CD3COOD d4. δ in ppm): from 2.55 to 2.90 (mf, 4H); 2.80 (s, 3H); from 2.95 to 3.30 (mf, 4H); from 3.30 to 3.60 (mf, 2H); 3.40 (dd, J=11.5 and 5.5 Hz, 1H); 3.69 (dd, J=11.5 and 7.5 Hz, 1H); 4.51 (mt, 1H)].

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction medium is concentrated under reduced pressure (2 kPa) at a temperature of about 55° C
  3. customThe residue obtained
  4. customis dried in an oven under vacuum (2 kPa) for 4 hours

Sources & evidence

ORD record
ord-d9ad0ec9ae704c49b15c7185548761b0
Source dataset
uspto-grants-2007_06
Patent number
US07227022B2

Reaction notes

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