Sodium borohydride → 1-Boc-4-(4-Methylaminobenzyl)piperazine

HRID 534726Notes

Reaction equation

C[C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[BH4-].[Na+]>>[CH3:16][NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:7][CH2:2][N:3]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][CH2:5]2)=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 468354511-Boc-4-(4-Methylaminobenzyl)piperazine

Conditions

Temperature: 50 °C

Procedure

The title compound was prepared from D11 using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. overnight prior to addition of sodium borohydride and no column chromatography was required. δH (CDCl3, 400 MHz) 7.11 (2H, d), 6.57 (2H, d), 3.69 (1H, br.s), 3.40 (6H, m), 2.83 (3H, s), 2.36 (4H, m), 1.45 (9H, s) [δ values corrected for incorrectly referenced TMS at 0.58 ppm on spectrum]. MS (ES+): 206.2, no molecular ion (MH+) observed.

Sources & evidence

ORD record: ord-4dca912e0f4b400cad2b05172d6e14e0
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853218B2

Reaction notes

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