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Acetonitrile → Tert-butyl 4-(4-chloro-1,3,5-triazin-2-yl)piperazine-1-carboxylate

HRID 2251210
Notes
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Reaction equation

HRID 2251210 reaction equation
ClN1[N:7]=[C:6]([Cl:8])C=CN1.[CH2:9]([N:11]([CH2:14]C)CC)C.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(OCC)(=O)C.C(#[N:37])C>[Cl-].[Na+].O>[C:19]([O:18][C:16]([N:23]1[CH2:24][CH2:25][N:26]([C:9]2[N:7]=[C:6]([Cl:8])[N:37]=[CH:14][N:11]=2)[CH2:27][CH2:28]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178478418HCID 178478418, compound

Product 1

HCID 86600711Tert-butyl 4-(4-chloro-1,3,5-triazin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents

1
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11 mmol of 2,4-dichlorotriazine (WO 02/083654) in 20 ml of acetonitrile was chilled and treated with 11 mmol of triethylamine and 11 mmol of N-BOC-piperazine. The reaction mixture was stirred for 2 hours at 0° C. then for 2 hours at room temperature. Addition of 100 ml brine and extraction with ethyl acetate yielded the crude product which was purified through trituration in ethyl acetate. MS (m/e): 300.3 (MH+, 100%)

Workup

  1. waitfor 2 hours at room temperature

Sources & evidence

ORD record
ord-9bd7fea4de2040bf8c26c3a795567624
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07319099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes