1-Hydroxybenzotriazole → tert-Butyl [2-(4-benzylpiperazin-1-yl)-2-oxoethyl]carbamate

HRID 1177945Notes

Reaction equation

HRID 1177945 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:44]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C.O>[C:10]([O:14][C:15](=[O:16])[NH:17][CH2:18][C:19]([N:54]1[CH2:55][CH2:56][N:51]([CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:52][CH2:53]1)=[O:21])([CH3:11])([CH3:12])[CH3:13]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 17750346tert-Butyl [2-(4-benzylpiperazin-1-yl)-2-oxoethyl]carbamateYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (22.14 g, 171.3 mmol) was added to a stirred solution of tert-butoxycarbonylamino-acetic acid (10 g, 57.1 mmol) in DMF (40 mL). HOBT (9.25 g, 68.5 mmol) and EDCI.HCl (12.61 g, 68.5 mmol) were then added at room temperature. After 2 minutes N-benzylpiperazine (12.1 g, 68.5 mmol) was added, and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 13.4 g (70.5% yield) of [2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester as white powder. 1H NMR (CDCl3): δ 7.3 (m, 5H), 5.5 (bs, 1H), 4.0 (d, 2H), 3.7-3.6 (t, 2H), 2.5 (s, 2H), 3.4 (t, 2H), 2.4 (s, 4H), 1.3 (s, 9H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac64ec04d5bc4cd18e89718f2fe3bb5b
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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