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

HRID 644702Notes

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) [6 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-b5b7ac2b07a044efb0b906538aa36c49
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700599B2

Reaction notes

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