Triethylamine → Hexamethylenetetramine

HRID 2237329Notes

Reaction equation

HRID 2237329 reaction equation
C[CH2:2][N:3]=[C:4]=[N:5][CH2:6]CCN(C)C.Cl.O[N:14]1C(=O)CCC1=O.[CH2:21]([N:23]([CH2:26]C)[CH2:24]C)C>ClCCl>[CH2:21]1[N:5]2[CH2:6][N:14]3[CH2:2][N:3]([CH2:4]2)[CH2:24][N:23]1[CH2:26]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 4101HexamethylenetetramineYield 895.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

C4 (197 mg, 0.201 mmol), EDC hydrochloride (77 mg, 0.401 mmol) and N-hydroxysuccinimide (35 mg, 0.301 mmol) were dissolved in anhydrous dichloromethane (30 ml) and activated ester formation left at room temperature for two hours under argon. To the solution was added E4 (300 mg, 0.211 mmol) and triethylamine (61 mg, 0.602 mmol) and the reaction left overnight at room temperature under argon. The solvents were removed, and the resulting residues purified by gradient silica column chromatography (3-7% methanol in dichloromethane) to yield the title compound as a colourless solid (378 mg, 78%). C119H209N11O37 requires 2384.5. Found ES+: MH22+, 1193.9, MH33+, 796.4. δH (CDCl3) 1.23 (46H, (CH2)19(CH2)2CO, (CH2)4CH), 1.44 (72H, br+m, (Me)3C, CH2CH2N, CH2CH2CO), 1.95 (1H, br, CH), 2.02-2.23 (30H, 10×s, MeCO), 2.17 (2H, t, (CH2)22CH2CO), 2.4-2.8 (4H, brm, CO(CH2)2CO), 2.83 (6H, s, MeN), 2.9-3.5 (32H, m, CH2N), 4.12 (2H, m, CH2OAc), 4.30 (2H, dt, CH2OAc), 5.20, 5.25 (2H, 2×d, CHOAcCO), 5.43, 5.60 (4H, 2×m, (CHOAc)2CHOAcCO), 5.71 (1H, br, (CH2)23CONH), 6.11 (1H, br, CO(CH2)2CONH), 7.18, 7.65 (2H, 2×t, N(CH2CH2NH)2.

Workup

  1. customThe solvents were removed
  2. customthe resulting residues purified by gradient silica column chromatography (3-7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-db298ee7f07048eb972f826d3456d2df
Source dataset
uspto-grants-2010_05
Patent number
US07718157B1

Reaction notes

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