Aluminium lithium hydride → HCID 68579061, compound

HRID 273086Notes

Reaction equation

HRID 273086 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH3:28])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1)[CH3:8]>O1CCCC1>[NH2:27][CH2:26][C:20]1([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][CH2:10][N:9]([CH2:7][CH3:8])[CH3:28])=[CH:15][CH:16]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68576156HCID 68576156, compound

Product 1

HCID 68579061HCID 68579061, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (9.93 ml of a 1M solution in tetrahydrofuran, 9.93 mmol) was added to a solution of 4-(4-{3-[ethyl(methyl)amino]propoxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile (2.0 g, 6.6 mmol) in tetrahydrofuran (10 ml) at 0° C. under N2. The reaction mixture was warmed to room temperature over 18 h and then quenched by the sequential addition of water (0.4 ml), 2M NaOH solution (0.4 ml) and water (0.4 ml). The mixture was filtered through arbocel and concentrated in vacuo to yield 3-{4-[4-(aminomethyl)tetrahydro-2H-pyran-4-yl]phenoxy}-N-ethyl-N-methylpropan-1-amine as a pale yellow oil (1.93 g, 6.3 mmol, 95%). 1H NMR (400 MHz CDCl3) δ 1.02-1.08 (t, 3H), 1.73-1.83 (m, 2H), 1.90-2.00 (m, 2H), 2.06-2.16 (m, 2H), 2.23 (s, 3H), 2.40-2.48 (q, 2H), 2.50-2.58 (t, 2H), 2.75 (s, 2H), 3.48-3.58 (m, 2H), 3.70-3.80 (m, 2H), 3.98-4.04 (t, 2H), 6.89 (d, 2H), 7.19 (d, 2H). LRMS APCI+ m/z 307 [MH]+.

Workup

  1. customquenched by the sequential addition of water (0.4 ml), 2M NaOH solution (0.4 ml) and water (0.4 ml)
  2. filtrationThe mixture was filtered through arbocel
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61b09e38bd674d6f80304ef200a93d58
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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