1-Piperonylpiperazine → HCID 59737378, compound

HRID 1907752Notes

Reaction equation

HRID 1907752 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:21][C:16]=2[O:15][CH2:14]1.[NH2:29][C:30]1[CH:35]=[C:34]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)[CH:33]=[CH:32][C:31]=1[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45]>C(Cl)Cl.N1C=CC=CC=1>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][N:23]3[CH2:24][CH2:25][N:26]([C:2]([NH:29][C:30]4[CH:35]=[C:34]([C:36]5[S:37][CH:38]=[CH:39][CH:40]=5)[CH:33]=[CH:32][C:31]=4[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:4])[CH2:27][CH2:28]3)=[CH:21][C:16]=2[O:15][CH2:14]1

Participants

6

Reactant 3

HCID 944261-PiperonylpiperazineHCID 94429TriphosgeneHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 59737378HCID 59737378, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of triphosgene (544 mg, 1.83 mmol, 1.05 eq.) in DCM (5 mL) stirred at 0° C. under nitrogen was treated with a solution of 1-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine (314, 1.16 g, 5.24 mmol) in anhydrous pyridine (7 mL), added dropwise over 5 min. The resulting mixture was stirred at 0° C. for 3 h and then at room temperature for 30 min, transferred with a syringe into a flask containing solid amine 4 (832 mg, 2.87 mmol), stirred at room temperature for 21 h, diluted with DCM, washed (saturated NaHCO3 then water), dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (elution with 5% isopropyl alcohol in DCM) gave title compound 315 (165 mg, 11% yield) as a yellow solid.

Workup

  1. additionadded dropwise over 5 min
  2. waitat room temperature for 30 min
  3. customtransferred with a syringe into a flask
  4. stirringstirred at room temperature for 21 h
  5. washwashed (saturated NaHCO3
  6. dry with materialwater), dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification
  10. washby flash column chromatography (elution with 5% isopropyl alcohol in DCM)

Sources & evidence

ORD record
ord-573f01ff574c4f1f93e3af7474ce7d8f
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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