Dicyclohexylamine → HCID 12887429, compound

HRID 877860Notes

Reaction equation

HRID 877860 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C.ClC(Cl)(O[C:25](=[O:31])OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH:8]1([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:25](=[O:31])[N:16]([CH:17]2[CH2:18][CH2:10][CH2:9][CH2:8][CH2:13]2)[CH:19]2[CH2:20][CH2:3][CH2:2][CH2:1][CH2:6]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 7582Dicyclohexylamine2×HCID 8471Triethylamine2×HCID 94429Triphosgene

Product 1

HCID 12887429HCID 12887429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dicyclohexylamine (3.9 mL, 19 mmol) and triethylamine (6 mL, 43 mmol) in THF (64 mL) was added dropwise to a stirred solution of triphosgene (1.99 g, 6.7 mmol) in THF (35 mL) at room temperature. The reaction mixture was stirred overnight. Then, a solution of dicyclohexylamine (3.9 mL, 18 mmol) and triethylamine (6 mL, 43 mmol) in THF (37 mL) was added. The reaction mixture was stirred overnight at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated to dryness, yielding tetracyclohexylurea as a yellow solid. Yield: 4.5 g (65%). A solution of oxalyl chloride in dichloromethane (1.1 mL, 13 mmol) was added to a stirred solution of the urea (4.5 g, 11 mmol) in THF (50 mL). The reaction mixture was evaporated to dryness after overnight heating to reflux. A solution of ammonia in methanol (5 mL, 35 mmol, 7 M) was added to a solution of the formed solid in THF (40 mL). The reaction mixture was heated to reflux overnight and evaporated to dryness. The product was neutralized and treated with aqueous sodium hydroxide solution. The organic layer was extracted with diethyl ether and dried over magnesium sulfate. Crystallization from hexanes yielded the desired guanidine as a brown solid. Yield: 2.9 g (64%). 13C NMR (CDCl3, 75 MHz): δ 25.4, 26.2, 31.8, 58.0, 156.2 ppm.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. temperatureat reflux temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-fa4b3258b3564ed39fd24f586ad1d0b3
Source dataset
uspto-grants-2015_03
Patent number
US08987393B2

Reaction notes

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