Hydrochloric Acid → (S)-2-amino-1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-3-(thiophen-2-yl)propan-1-one hydrochloride

HRID 447151Notes

Reaction equation

HRID 447151 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:32])[C@@H:17]([NH:24]C(=O)OC(C)(C)C)[CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:11]1.[ClH:33]>O1CCOCC1>[ClH:33].[NH2:24][C@@H:17]([CH2:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH2:11][CH2:12]1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67235987(S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

Product 1

HCID 67236161(S)-2-amino-1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-3-(thiophen-2-yl)propan-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

(S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (367.5 mg, 0.805 mmol) was dissolved in 1,4-dioxane (5 mL) and treated with 4N hydrogen chloride in 1,4-dioxane (5 mL, 12.0 mmol). The resulting mixture was stirred at room temperature for 3 h, then additional 4N HCl in 1,4-dioxane (1 mL) was added and the resulting mixture stirred for 18 h. The resulting solid was collected by decantation, washed with 1,4-dioxane, and purified by recrystallization from an isopropanol-diethyl ether mixture to yield the title compound as an off-white solid.

Workup

  1. stirringthe resulting mixture stirred for 18 h
  2. customThe resulting solid was collected by decantation
  3. washwashed with 1,4-dioxane
  4. custompurified by recrystallization from an isopropanol-diethyl ether mixture

Sources & evidence

ORD record
ord-299db8ada9b14d43bf3fa706ef458b99
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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