Aluminium lithium hydride → HCID 66835897, compound

HRID 2404436Notes

Reaction equation

HRID 2404436 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[S:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[CH:11]([O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 66835898HCID 66835898, compound

Product 1

HCID 66835897HCID 66835897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]benzoic acid ethyl ester (0.55 g, example 206) in tetrahydrofurane (10 mL) is treated with lithium aluminum hydride (76 mg) at room temperature for 1 h. Two other additions of lithium aluminum hydride (76 mg each) allow a complete conversion. The mixture is then hydrolyzed with water (178 μL), 5% sodium hydroxide (178 μL) and water (535 μL), filtered through a pad of clarcel and concentrated under reduced pressure. The residue is purified over silica gel (dichloromethane/methanol/ammonia 95/5/0.5) to afford {3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}methanol which is then converted into its oxalate salt in acetone to give {3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}methanol, oxalate.

Workup

  1. filtrationhydrolyzed with water (178 μL), 5% sodium hydroxide (178 μL) and water (535 μL), filtered through a pad of clarcel
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified over silica gel (dichloromethane/methanol/ammonia 95/5/0.5)

Sources & evidence

ORD record
ord-411867aaec444afc934fc0000a0bf6d7
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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