Hexylamine → HCID 57554480, compound

HRID 551934Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH:15]=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:21]([NH2:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][NH:27][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 8102Hexylamine

HCID 860770722-[(4-Butylphenyl)ethynyl]benzaldehyde

Product 1

HCID 57554480HCID 57554480, compoundYield 12%

Procedure

The title compound was prepared following procedure described in example 19, step b) from 2-[(4-butylphenyl)ethynyl]benzaldehyde (1.12 g, 4.28 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and n-hexylamine (Aldrich, 294 μl, 5.13 mmol). Purification of the crude product by flash chromatography on silicagel (DCM/MeOH/NH4OH 98/2/1) gave 174 mg (12%) of the title compound. HPLC, Rt: 4.39 min purity: 91.6%). LC/MS, M+(ESI): 348.4. 1HNMR (CDCl3) δ: 0.82 (t, J=6.8 Hz, 3H), 0.91 (t, J=7.3 Hz, 3H), 1.23-1.40 (m, 8H), 1.46-1.64 (m, 4H), 2.25 (m, 1H), 2.62 (t, J=7.5 Hz, 4H), 4.00 (s, 2H), 7.15 (d, J=8.3 Hz, 2H), 7.17-7.26 (m, 2H), 7.39 (m, 1H), 7.42 (d, J=8.3 Hz, 2H), 7.50 (dd, J=7.3, 1.7 Hz, 1H).

Workup

customThe title compound was prepared following procedure
customPurification of the crude product by flash chromatography on silicagel (DCM/MeOH/NH4OH 98/2/1)

Sources & evidence

ORD record: ord-3212fbdb660741189a312a84dd48291d
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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