Hydrochloric Acid → N-(2-Aminoethyl)-N'-[1-(2-pyridinyl)-4-piperidinyl]urea dihydrochloride

HRID 353646Notes

Reaction equation

HRID 353646 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([NH:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[O:15])[CH2:9][CH2:8]1.[ClH:27]>C(OCC)(=O)C>[ClH:27].[ClH:27].[NH2:19][CH2:18][CH2:17][NH:16][C:14]([NH:13][CH:10]1[CH2:11][CH2:12][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9]1)=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9925235tert-Butyl 2-[({[1-(2-pyridinyl)-4-piperidinyl]amino}carbonyl)amino]ethylcarbamate

Product 1

HCID 9967555N-(2-Aminoethyl)-N'-[1-(2-pyridinyl)-4-piperidinyl]urea dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of tert-butyl 2-[({[1-(2-pyridinyl)-4-piperidinyl]amino}carbonyl)amino]ethylcarbamate (Preparation 72) (20.6 g, 0.0567 moles) in ethyl acetate (115 ml) under an atmosphere of nitrogen was added a saturated solution of hydrogen chloride in ethyl acetate (115 ml) and the resulting thick slurry was stirred at ambient temperature for 2 hours. The solid was collected by filtration and the filter cake was washed with ethyl acetate (2×50 ml) after which it was dried in vacuo at 50° C. to give the title compound (21.0 g) as a hygroscopic colourless solid, m.p. 112-120° C.

Workup

  1. filtrationThe solid was collected by filtration
  2. washthe filter cake was washed with ethyl acetate (2×50 ml) after which it
  3. customwas dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-52b353d5109f4f4a9b3c3da32dcd2ec0
Source dataset
uspto-grants-2004_06
Patent number
US06753322B2

Reaction notes

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