Morpholine → HCID 66855611, compound

HRID 1170853Notes

Reaction equation

HRID 1170853 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[C:14]1([N:20]2[C:28]3[CH2:27][CH2:26][CH2:25][C:24](=[CH:29][C:30]([OH:32])=O)[C:23]=3[CH:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(Cl)Cl>[C:14]1([N:20]2[C:28]3[CH2:27][CH2:26][CH2:25][C:24](=[CH:29][C:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[O:32])[C:23]=3[CH:22]=[N:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66857956HCID 66857956, compound

Product 1

HCID 66855611HCID 66855611, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.054 mL, 0.39 mmol) and ethyl chloroformate (0.037 mL, 0.30 mmol) are added to a solution of a mixture of E/Z of 2-(1,5,6,7-tetrahydro-1-phenyl-4H-indazol-4-ylidene)acetic acid (100 mg, 0.39 mmol) in CH2Cl2 (5 mL) cooled to 0° C. and is stirred for 45 minutes at 0° C. Then morpholine (0.034 mL, 0.39 mmol) is added following the reaction by means of TLC. The solution is washed with diluted NaOH, the organic phase is separated, dried and evaporated under reduced pressure. The resulting crude product is purified by means of silica gel chromatography giving an E/Z mixture (80/20) of 4-(2-(1-phenyl-6,7-dihydro-1H-indazol-4(5H)-ylidene)acetyl)morpholine (40 mg, 0.12 mmol, 32%).

Workup

  1. customthe reaction by means of TLC
  2. washThe solution is washed with diluted NaOH
  3. customthe organic phase is separated
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe resulting crude product is purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-bb15328ac77e4e2c9abc2c678a28f95e
Source dataset
uspto-grants-2010_11
Patent number
US07829559B2

Reaction notes

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