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

HRID 259483

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 6 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-f85731e5adc4449cbc7c46040f22e5c5
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04038312

Linked notes

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