Triethylamine → HCID 68928242, compound

HRID 1027453Notes

Reaction equation

HRID 1027453 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]1[CH3:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([N:34]1[CH2:39][CH2:38][NH:37][C@@H:36]([CH3:40])[CH2:35]1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Br[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C(N(CC)CC)C>CC#N>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:16][C@@H:15]1[CH3:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH:21]([N:34]1[CH2:39][CH2:38][N:37]([CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@@H:36]([CH3:40])[CH2:35]1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 68930909HCID 68930909, compoundHCID 68933826(2S)-1-(Diphenylmethyl)-2-methylpiperazine

Product 2

HCID 68928242HCID 68928242, compoundHCID 68933233HCID 68933233, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of a mixture of (S)-1-benzhydryl-2-methylpiperazine and (S)-1-benzhydryl-3-methylpiperazine (490 mg, 1.839 mmol) in 25 mL of MeCN was added tert-butyl bromoacetate (356 μl, 2.207 mmol), followed by slow addition of triethylamine (384 μl, 2759 μmol). The reaction mixture was stirred at rt overnight. The solution was evaporated to dryness and the residual was submitted to flash chromatography (SiO2, DCM to DCM/EtOAc=100:3 to 100:5 to 100:10) to give (S)-tert-butyl 2-(4-benzhydryl-3-methylpiperazin-1-yl)acetate as a colorless oil and (S)-tert-butyl 2-(4-benzhydryl-2-methylpiperazin-1-yl)acetate as a colorless oil.

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-2fa6373518f449ca9fc61de0f80787bd
Source dataset
uspto-grants-2014_05
Patent number
US08735383B2

Reaction notes

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