Dimethylamine → Hexahydro-1H,4H,7H-3a,6a,9a-triaza-9b-phosphaphenalene

HRID 1973177

Reaction equation

[NH:1]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH2:2]1.CNC.CN(C)[P:18](N(C)C)N(C)C>>[N:1]12[P:18]3[N:9]([CH2:8][CH2:7][CH2:6][N:5]3[CH2:4][CH2:3][CH2:2]1)[CH2:10][CH2:11][CH2:12]2

Participants

Reactant 3

HCID 674Dimethylamine

HCID 15355Hexamethylphosphorous triamide

HCID 4707781,5,9-Triazacyclododecane

Product 1

HCID 333382Hexahydro-1H,4H,7H-3a,6a,9a-triaza-9b-phosphaphenaleneYield 76%

Procedure

A mixture of 4.20 g of 1,5,9-triazacyclododecane and 4.00 g of hexamethylphosphorous triamide is heated at 100° C for about six hours, by which time evolution of dimethylamine is complete. Distillation under reduced pressure gives 3.70 g (76%) of 1,5,9-triaza-13-phosphatricyclo-[7.3.1.05,13 ]tridecane as a clear, colorless liquid which boils at 104°-135° C at 0.60 mm. The product solidifies at room temperature. Its infrared absorption spectrum (neat) shows absorptions at 3.5, 6.85, 7.01, 7.52, 7.73, 8.00, 8.27, 8.66, 8.90, 9.02, 9.36, 9.56, 10.27, 10.89, 11.42, 11.73, 11.97 and 14.7 μ. The mass spectrum shows an M+ ion at 199; measured mass, 199.1264; calc'd, 199.1238.

Workup

distillationDistillation under reduced pressure

Sources & evidence

ORD record: ord-ea1c9badf517452ebff33d295102bd0d
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03996276

Linked notes

Loading…