Butylamine → HCID 18427961, compound

HRID 1279386Notes

Reaction equation

[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH:13](C)[C:14]#[CH:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.I[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[CH2:27](N)CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]#[C:27][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[CH2:11][CH2:12]2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(4-methylbenzyl)-1-(1-butyn-3-yl)piperidine (400 mg, 1.66 mmol) and 4-iodophenol (347 mg 1.57 mmol) in 10 mL of butylamine is added 80 mg of Pd(PPh3)4. The resulting solution is allowed to stir at 55° C. for 24 hr. The solvent is evaporated in vacuo and the residue is purified by flash chromatography (20% EtOAc in hexane) to give 150 mg (27%) of the title product as a brown oil. 1H NMR (CDCl3) 1.34 (m, 2 H), 1.50 (m, 1 H), 1.65 (d, J=11.7 Hz, 2 H), 2.08 (t, J=12.0 Hz, 2 H), 2.33 (s, 3 H), 2.47 (d, J=6.9 Hz, 2 H), 2.60 (t, J=7.2 Hz, 2 H), 2.68 (t, J=7.5 Hz, 2 H), 3.02 (d, J=11.1 Hz, 2 H), 3.49 (brs, 1 H), 6.68 (d, J=8.1 Hz, 2 H), 7.01 (d, J=7.5 Hz, 2 H), 7.08 (d, J=7.5 Hz, 2 H), 7.20 (d, J=8.1 Hz, 2 H).

Workup

customThe solvent is evaporated in vacuo
customthe residue is purified by flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record: ord-1b9965ecad124c8fba917be7cd7f676d
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448270B1

Reaction notes

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