1,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylate → (S)-3-benzyl-1-(4-methoxy-3-(1-methylpiperidin-4-yloxy)phenyl)piperazine

HRID 1423110Notes

Reaction equation

HRID 1423110 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:15]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.C(OC([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O)(C)(C)C>>[CH2:31]([C@@H:26]1[NH:25][CH2:30][CH2:29][N:28]([C:2]2[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([O:7][CH:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)[CH:15]=2)[CH2:27]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylateHCID 581891774-(5-Bromo-2-methoxy-phenoxy)-1-methyl-piperidine

Product 1

HCID 52918524(S)-3-benzyl-1-(4-methoxy-3-(1-methylpiperidin-4-yloxy)phenyl)piperazine

Procedure

The title compound was prepared by the method outlined for Example 1 using 4-(5-bromo-2-methoxy-phenoxy)-1-methyl-piperidine as the aryl halide and 2(S)-benzyl-piperazine-1-carboxylic acid tert-butyl ester as the amine component. The title compound was isolated as an orange oil. 1H NMR (MeOH-d4) 7.33-7.29 (m, 2H), 7.25-7.22 (m, 3H), 6.85 (d, J=8.8, 1H), 6.55 (d, J=2.8, 1H), 6.50 (dd, J=8.8, 2.8, 1H), 4.24 (m, 1H), 3.74 (s, 3H), 3.35-3.27 (m, 2H), 3.05-3.00 (m, 2H), 2.91-2.85 (m, 1H), 2.74-2.65 (m, 5H), 2.36 (m, 3H), 2.28 (s, 3H), 1.90 (m, 2H), 1.78 (m, 2H). LC/MS (Method B) 0.97 min, [M+1]+ 396.

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-2120c51ffe5b453495677f9bf635dac4
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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