Morpholine → HCID 22147728, compound

HRID 1386909Notes

Reaction equation

HRID 1386909 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7](C(O)=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:14].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18]C1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH:38]1CC[O:41][CH2:40][CH2:39]1>C(Cl)Cl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:14].[NH:38]1[CH2:18][CH:19]([C:20]([NH2:16])=[O:21])[O:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 22147713HCID 22147713, compound

Product 1

HCID 22147728HCID 22147728, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Tetralone-6-carboxylic acid, ethylene ketal (395 mg, 2.07 mmol) was codissolved in CH2Cl2 (50 mL) with N-hydroxysuccinimide (260 mg, 2.76 mmol) at 0° C. and treated with a slight excess of 1,3-dicyclohexylcarbodiimide (502 mg, 2.50 mmol). The mixture was allowed to warm to ambient temperature over 30 minutes, during which time a fine white precipitate formed. Morpholine (0.91 mL, 10.4 mmol, d=0.998) was added and the solution stirred at ambient temperature for 16 hours. The suspended urea was filtered away and the solution concentrated in vacuo to a colorless oil. The oil was applied to a silica flash chromatography column and eluted with 50-100% EtOAc in hexanes to yield 323 mg (51%) of 2-tetralone-6-morpholinamide, ethylene ketal as a slowly crystallizing solid, clean by NMR, TLC.

Workup

  1. customformed
  2. filtrationThe suspended urea was filtered away
  3. concentrationthe solution concentrated in vacuo to a colorless oil
  4. washeluted with 50-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-b9b5947437af4797b230a0f61e872c48
Source dataset
uspto-grants-2001_07
Patent number
US06265581B1

Reaction notes

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