Morpholine → HCID 66855611, compound

HRID 1943608Notes

Reaction equation

HRID 1943608 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-c2f9c5ff8d1c435b837e11de43b71a90
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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