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4-Methylmorpholine → HCID 67189501, compound

HRID 735951
Notes
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Reaction equation

HRID 735951 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[N:19]=2)=[CH:14][CH:13]=1.CN1CC[O:38][CH2:37][CH2:36]1.CC[C:43]([C:45](Cl)=[O:46])=[O:44]>C(Cl)Cl>[CH2:37]([O:38][C:43](=[O:44])[C:45]([N:10]([CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[N:19]=2)=[CH:14][CH:13]=1)=[O:46])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 11007880Butanoyl chloride, 2-oxo-HCID 67187358N-[2-(2-fluorophenyl)ethyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

Product 1

HCID 67189501HCID 67189501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N-[2-(2-fluorophenyl)ethyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine (45.1 mg, 0.1 mmol) in anhydrous DCM (0.6 mL) was added the morpholinomethyl polystyrene resin (Novabiochem, HL, 39.5 mg, 0.15 mmol, 3.8 mmol/g) and the resulting mixture was cooled at 0° C. Ethyloxalyl chloride (4.7 mg, 0.13 mmol) in anhydrous DCM (0.4 mL) was added. The reaction mixture was stirred for 2 h at rt, then the PL-AMS-Resin (Polymer Laboratories, 52 mg, 0.1 mmol, 1.93 mmol/g) was added and the mixture stirred for 1.5 h. The resins were filtered off, washed with DCM, and the filtrates were concentrated under vacuum to afford the title compound as an oil.

Workup

  1. additionthe PL-AMS-Resin (Polymer Laboratories, 52 mg, 0.1 mmol, 1.93 mmol/g) was added
  2. stirringthe mixture stirred for 1.5 h
  3. filtrationThe resins were filtered off
  4. washwashed with DCM
  5. concentrationthe filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-34ccf1d230d5473f93d155ea0aad6f8b
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592477B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes