4-Methylmorpholine → HCID 86738329, compound

HRID 2285578Notes

Reaction equation

HRID 2285578 reaction equation
[C:1]1([CH2:7][C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12](O)=O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CC[O:22]CC1.ClC(OCC(C)C)=O.[NH2:33][CH2:34][C:35]([NH2:38])([CH3:37])[CH3:36]>O.C(Cl)(Cl)Cl>[NH2:38][C:35]([CH3:37])([CH3:36])[CH2:34][N:33]1[CH2:12][CH2:11][CH2:15][C@H:16]1[C:17]([NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:22]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 131282-MethylpropylenediamineHCID 62365Isobutyl chloroformateHCID 6986012752-38-7

Product 1

HCID 86738329HCID 86738329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-23 °C

Procedure

A mixture of N-phenylacetyl-proline (17.4 g.), N-methylmorpholine (7.85 ml.) and analytical grade chloroform (60 ml.) was stirred at room-temperature for 5 minutes. After cooling to -23° C., isobutyl chloroformate (9.23 ml.) was added rapidly during 1 minute. An exothermic reaction occurred and the temperature rose to -15° C. After a further 1 minute of stirring, 1,2-diamino-2-methylpropane (7.86 ml.) was added rapidly and the temperature was allowed to rise to room-temperature with stirring during 2 hours. The mixture was then poured into water (50 ml.) and the organic layer separated and discarded. The aqueous layer was basified (solid potassium carbonate) and extracted with chloroform (4×100 ml.). The chloroform extracts were dried (MgSO4) and evaporated under high vacuum to give N1 -(2-amino-2-methylpropyl)-N2 -phenylacetylprolinamide as an oil (15.5 g.); NMR (δ) (CDCl3): 7.7-6.7 (6H, complex, aromatic H+NHCO); 4.5 (1H, complex, =N--CH--CO); 3.8-2.7 (6H, complex CH2N+PhCH2); 3.65 (singlet, PhCH2); 2.4-1.6 (6H, complex, CH2CH2CH+NH2); and 1.0 [6H, singlet, C(CH3)2 ].

Workup

  1. customAn exothermic reaction
  2. customrose to -15° C
  3. stirringAfter a further 1 minute of stirring
  4. stirringwith stirring during 2 hours
  5. customthe organic layer separated
  6. extractionextracted with chloroform (4×100 ml.)
  7. dry with materialThe chloroform extracts were dried (MgSO4)
  8. customevaporated under high vacuum

Sources & evidence

ORD record
ord-cbe3e308c1c942989a6eb4c829498a14
Source dataset
uspto-grants-1982_04
Patent number
US04323575

Reaction notes

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