4-Methylmorpholine → N-Boc sarcosine piperonylamide

HRID 352616Notes

Reaction equation

HRID 352616 reaction equation
ClC(OCC(C)C)=[O:3].[C:9]([N:16]([CH2:18][C:19]([OH:21])=[O:20])[CH3:17])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CN1CCOCC1.[CH2:29]([NH2:39])[C:30]1[CH:38]=[CH:37][C:36]2[O:35][CH2:34][O:33][C:32]=2[CH:31]=1>C1COCC1>[C:29]([NH2:39])(=[O:3])[C:30]1[CH:38]=[CH:37][C:36]2[O:35][CH2:34][O:33][C:32]=2[CH:31]=1.[C:9]([N:16]([CH2:18][C:19]([OH:21])=[O:20])[CH3:17])([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

Product 1

HCID 86586337N-Boc sarcosine piperonylamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (226 μL, 1.73 mmol) was added to a solution of N-Boc sarcosine (1.73 mmol) and N-methylmorpholine (192 μL, 1.73 mmol) in THF. After two minutes, piperonylamine (216 mL, 1.73 mmol) was added and the mixture allowed to warm to room temperature. After thirty minutes, the reaction mixture was passed through a bed of Celite and all volatiles were removed under reduced pressure to yield N-Boc sarcosine piperonyl amide (531 mg, 95%) as a white solid. 1H NMR: (CDCl3) δ2.41 (s, 3), 3.28 (s, 2), 4.39 (d, 2), 5.95 (s, 2), 6.80 (m, 3), 7.43 (bs, 1), 904 (bs, 1).

Workup

  1. waitAfter thirty minutes
  2. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-8314f2f38c8b42ce8abc2e46c10439f3
Source dataset
uspto-grants-2004_06
Patent number
US06747031B2

Reaction notes

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