Ammonia → (4-(2-(azepan-1-yl)ethoxy)phenyl)methanol

HRID 1949990Notes

Reaction equation

HRID 1949990 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].N>O1CCCC1>[N:14]1([CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 66625442HCID 66625442, compound

Product 1

HCID 9816367(4-(2-(azepan-1-yl)ethoxy)phenyl)methanolYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(2-azepan-1-ylethoxy)benzoic acid ethyl ester (6.0 g) in tetrahydrofuran (60 ml) was added lithium aluminum hydride (1.5 g) under a nitrogen atmosphere, the solution was stirred overnight at room temperature, tetrahydrofuran and aqueous ammonia were then sequentially added thereto on an ice bath, the solution was filtered through celite pad, the solvent was evaporated in vacuo to provide [4-(2-azepan-1-ylethoxy)phenyl]methanol (3.6 g). The title compound (194 mg) was obtained according to an analogous synthetic method to Preparation Example 13 using the above compound (200 mg).

Workup

  1. filtrationon an ice bath, the solution was filtered through celite pad
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b67cf45bd51c49bd9276c0539e728d4a
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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