Water → HCID 15675407, compound

HRID 1461278Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[O:21][C:20]([C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=O)=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[N+]=[N-].O.[OH-].[Na+]>O1CCCC1>[NH2:7][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[O:21][C:20]([CH2:22][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

In 100 ml of dry tetrahydrofuran was suspended 1.1 g (28.8 mmol) of lithium aluminum hydride, and under nitrogen stream a solution of 2.28 g (7.2 mmol) of Compound v in 50 ml of dry tetrahydrofuran was added dropwise at room temperature. After completion of dropwise addition, the mixture was heated under reflux for 20 hours. The reaction mixture was ice-cooled and 2.2 ml of water, 1.1 ml of 20% aqueous sodium hydroxide solution and 5.5 ml of water were serially added gradually. The mixture was stirred at 0° C. for 30 minutes. The insolubles were then filtered off, the filtrate was concentrated under reduced pressure, and the residue was subjected to vacuum distillation (160°-180° C./1 mmHg) to give 1.82 g (91.5%) of 2-(4-amino-piperidinomethyl)-5-piperidinomethylfuran (Compound w) as light yellow oil.

Workup

additionwas added dropwise at room temperature
additionAfter completion of dropwise addition
temperaturethe mixture was heated
temperatureunder reflux for 20 hours
temperaturecooled
filtrationThe insolubles were then filtered off
concentrationthe filtrate was concentrated under reduced pressure
distillationthe residue was subjected to vacuum distillation (160°-180° C./1 mmHg)

Sources & evidence

ORD record: ord-f0b6fd8995f940049210afd2531fa516
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075301

Reaction notes

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