Water → HCID 57637965, compound

HRID 2111481Notes

Reaction equation

HRID 2111481 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:37]=[CH:36][C:23]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:29]([C:30](OC)=[O:31])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(OC(C)(C)C)=O.O.[OH-].[Na+]>C1COCC1>[CH3:7][N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:37]=[CH:36][C:23]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:29]([CH2:30][OH:31])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57637614HCID 57637614, compound

Product 1

HCID 57637965HCID 57637965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a slurry of LiAlH4 (4 equivalents) in dry THF, cooled to 0° C. under N2, was slowly added drop-wise a solution of methyl 4-[4-(1-BOC-piperazin-4-yl)phenoxymethyl]benzoate (1 equivalent) in dry THF. Once the addition was complete, the slurry was heated to reflux at 80° C. for 1 hour. The slurry was subsequently cooled to 0° C. and treated with water, 10% aq. NaOH and with water again. The resulting solids were filtered, and the filtrate was diluted with chloroform, washed with brine, dried over MgSO4 and concentrated, providing the crude 4-[4-(4-methylpiperazin-1-yl)phenoxymethyl]benzyl alcohol which was used without purification.

Workup

  1. additionOnce the addition
  2. temperaturethe slurry was heated
  3. temperatureThe slurry was subsequently cooled to 0° C.
  4. filtrationThe resulting solids were filtered
  5. additionthe filtrate was diluted with chloroform
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1763e142eb1a4ce5ab78662cf5416738
Source dataset
uspto-grants-2009_04
Patent number
US07521062B2

Reaction notes

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