4-Methylmorpholine → N-Boc sarcosine piperonylamide

HRID 1822768Notes

Reaction equation

HRID 1822768 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

Another specific example of the synthesis, applied to a compound of formula I in which R9 is —CH3 and R4 is —C(O)NHR5, is provided: Isobutyl chloroformate (226 mL, 1.73 mmol) was added to a solution of N-Boc sarcosine (1.73 mmol) and N-methyl morpholine (192 mL, 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) δ 2.41, 3H, s; 3.28, 2H, s; 4.39, 2H, d; 5.95, 2H, s; 6.80, 3H, m; 7.43, 1H, bs; 9.04, 1H, bs.]

Workup

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

Sources & evidence

ORD record
ord-dcab7a75bbb740cbbeafc3551f7ec0b3
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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