Water → (1,4-Dibenzylpiperazin-2-yl)methanol

HRID 1161863Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)C.O.[OH-].[Na+]>C1COCC1>[CH2:25]([N:13]1[CH2:14][CH2:15][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH:12]1[CH2:10][OH:9])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium aluminium hydride (1M in THF) (4 mL, 3.93 mmol) was added to a stirred solution of 1,4-dibenzylpiperazine-2-carboxylic acid ethyl ester (1.33 g, 3.93 mmol) in THF (25 mL) cooled to −78° C. under a nitrogen atmosphere. Water (145 μL), NaOH (aq.) (10 wt %, 145 μL) and water (450 μL) was added at 45 min intervals. The reaction mixture was filtered through a pad of celite and solvent evaporated under reduced pressure to afford (1,4-dibenzylpiperazin-2-yl)methanol (1.16 g, 3.93 mmol, 100%) as a pale yellow oil. Data for (1,4-dibenzylpiperazin-2-yl)methanol: MS (ESI) m/z: 298 ([M+H]+).

Workup

filtrationThe reaction mixture was filtered through a pad of celite and solvent
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-0fa1a867b3b44c87b65d0ee36790fa95
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820649B2

Reaction notes

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