Sodium Hydroxide → [4-(Morpholin-4-ylmethyl)phenyl]methanamine

HRID 1191000

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[OH-].[Na+]>C1COCC1.O.C(OCC)C>[N:7]1([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, add lithium aluminum hydride (1.13 g, 29.7 mmol) to THF (50 mL) at 0° C. followed by a solution of 4-(morpholin-4-ylmethyl)-benzonitrile (2 g, 9.89 mmol) in THF (10 mL). Stir at 0° C. for 1 h and at room temperature overnight. Cool the mixture to 0° C., and carefully add water (1.15 mL). Add diethyl ether (125 mL), 3N aqueous NaOH (1.15 mL), water (3.45 mL), and stir for 1 h at room temperature. Filter the solid residue and concentrate the filtrate in vacuo to obtain the title compound as a colorless oil (1.87 g, 94%). MS (APCI+) m/z: 207 (M+H)+.

Workup

temperatureCool the mixture to 0° C.
filtrationFilter the solid residue
concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record: ord-38763a18346d4bdb8e4e4c28e7e940d1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680091B2

Linked notes

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