4-Methylmorpholine → HCID 67189501, compound

HRID 735951Notes

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]

Participants

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

additionthe PL-AMS-Resin (Polymer Laboratories, 52 mg, 0.1 mmol, 1.93 mmol/g) was added
stirringthe mixture stirred for 1.5 h
filtrationThe resins were filtered off
washwashed with DCM
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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