Sodium Hydroxide → HCID 18668757, compound

HRID 1058613Notes

Reaction equation

HRID 1058613 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[N+]=[N-].[OH-].[Na+]>O1CCCC1>[NH2:7][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15480811HCID 15480811, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18668757HCID 18668757, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 4.70 g of lithium aluminium hydride in 250 ml of dried tetrahydrofuran, a solution of 47.7 g of 4-azidomethyl-N-triphenylmethylpiperidine in 250 ml of dried tetrahydrofuran was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added dropwise with a mixture of tetrahydrofuran and 10% aqueous sodium hydroxide solution under ice-cooling. An insoluble matter in the mixture was filtered off, and washed with tetrahydrofuran. The filtrate and the washings were combined and concentrated to give 48.1 g of a colorless liquid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationAn insoluble matter in the mixture was filtered off
  4. washwashed with tetrahydrofuran
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c4cb6fb3c86c45deb1240bec6f478e14
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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