Cyclopropylamine → N-(3-methoxy-5-(3-methoxypropoxy)benzyl)cyclopropanamine

HRID 1698358Notes

Reaction equation

HRID 1698358 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=1)[CH:6]=O.[CH:17]1([NH2:20])[CH2:19][CH2:18]1>CC#N>[CH:17]1([NH:20][CH2:6][C:5]2[CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 598177593-Methoxy-5-(3-methoxy-propoxy)-benzaldehyde

Product 1

HCID 59817709N-(3-methoxy-5-(3-methoxypropoxy)benzyl)cyclopropanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The title compound is synthesized by reductive amination of 3-Methoxy-5-(3-methoxy-propoxy)-benzaldehyde (2.50 g, 11.1 mmol) with cyclopropylamine (855 mg, 15.0 mmol) analogously to the preparation of Example 152. Yellow oil; MS: 266 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 2.48 min.

Workup

  1. custom2.48 min.

Sources & evidence

ORD record
ord-d762280aee18431fbee256841a2f242d
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

Loading…