Aluminium lithium hydride → [2-Morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine

HRID 1479830Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[N:8]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH2:13][NH2:14])[CH:10]=[C:9]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:19][CH:20]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

The nitrile 26D (2 g, 5.7 mmol) dissolved in 50 ml of diethyl ether was added dropwise to a mixture of LiAlH4 (434 mg, 2 equiv.) in diethyl ether (60 mL) stirred at 0° C. Then the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed by water addition at 0° C., the solid formed was filtered, washed with Et2O and the filtrate was dried over Na2SO4 and evaporated to dryness to obtain 1.3 g of the amine 27D as a yellow oil. Yield=65% 1HNMR (DMSO, 400 MHz) δ 3.30 (2H, bs), 3.51 (4H, m), 3.76 (6H, m), 6.80 (1H, s), 7.29 (1H, s), 7.42 (2H, d, J=8 Hz), 8.18 (2H, dd)

Workup

stirringThen the mixture was stirred at room temperature overnight
customThe excess of LiAlH4 was destroyed by water addition at 0° C.
customthe solid formed
filtrationwas filtered
washwashed with Et2O
dry with materialthe filtrate was dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-5a1a41e659594c1bb881592cbcf409a7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

Loading…