1-Azido-4-[3-(1-piperidinylmethyl)phenoxy]-2-butanol → 1-Amino-4-{3-[(piperidin-1-yl)methyl]phenoxy}butan-2-ol

HRID 2164742Notes

Reaction equation

HRID 2164742 reaction equation
[N:1]([CH2:4][CH:5]([OH:22])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:10]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][CH2:4][CH:5]([OH:22])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:10]=1

Participants

4

Reactant 2

HCID 202460071-Azido-4-[3-(1-piperidinylmethyl)phenoxy]-2-butanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 202460151-Amino-4-{3-[(piperidin-1-yl)methyl]phenoxy}butan-2-olYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-azido-4[3-(1-piperidinylmethyl)phenoxy]-2-butanol (10 g) in dry tetrahydrofuran (100 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (4 g) in tetrahydrofuran (200 ml) under nitrogen. The resulting mixture was stirred at room temperature for 1 h and quenched with water (4 ml), followed by 15% sodium hydroxide (4 ml) and water (12 ml). The mixture was then filtered and the residue washed with tetrahydrofuran (50 ml). The combined filtrate was evaporated to give the title compound (7.5 g) as a pale pink oil.

Workup

  1. customquenched with water (4 ml)
  2. filtrationThe mixture was then filtered
  3. washthe residue washed with tetrahydrofuran (50 ml)
  4. customThe combined filtrate was evaporated

Sources & evidence

ORD record
ord-c6b2e109218840cebbec43ac0528fdd2
Source dataset
uspto-grants-1985_03
Patent number
US04507296

Reaction notes

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