Cyclopropanemethanamine → 4-[(Cyclopropylmethyl)amino]-N,N-diethyl-3-nitrobenzamide

HRID 1796465Notes

Reaction equation

HRID 1796465 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[CH:18]1([CH2:21][NH2:22])[CH2:20][CH2:19]1>C(O)C>[CH:18]1([CH2:21][NH:22][C:8]2[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:16][CH3:17])[CH2:1][CH3:2])=[O:15])=[CH:6][C:7]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 221814094-[(Cyclopropylmethyl)amino]-N,N-diethyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure 2B: N,N-diethyl-4-fluoro-3-nitrobenzamide (0.823 g, 3.42 mmol) and cyclopropylmethanamine (0.39 mL, 4.50 mmol) in 80% aqueous ethanol (17 mL) were stirred at 85° C. for 16 h. The crude product (1.00 g), an orange solid, was used in subsequent steps. 1H-NMR (CD3OD): δ 8.23 (d, J=2.0 Hz, 1H), 7.55 (dd, J=9.2 Hz, J=2.0 Hz, 1H), 7.09 (d, J=9.2 Hz, 1H), 3.47 (br s, 3H), 3.31 (q, J=2.0 Hz, 2H), 3.27 (d, J=6.4 Hz, 2H), 1.23 (overlapping t and m, J=7.0 Hz, 7H), 0.68–0.60 (m, 2H), 0.40–0.34 (m, 2H). MS (ESI) (M+H)+=292.

Sources & evidence

ORD record
ord-85d5e2d2a4a74ee4896bdd94fc17f615
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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