Hydrochloric Acid → HCID 10039179, compound

HRID 1646933Notes

Reaction equation

Cl[C:2]1[C:3]([C:8]2([OH:16])[CH:13]3[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.Cl>C(O)CCC>[CH2:8]([O:16][C:2]1[C:3]([C:8]2([OH:16])[CH:13]3[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1)[CH2:13][CH2:12][CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 40 ml of butanol that had reacted with 0.5 g of Na (0.022 mol) was added 0.78 g of (7) (0.033 mol). The reaction was heated to 60° C. for 1.5 h and the cooled reaction treated with 6 ml of 5 N HCl. The butanol was azeotroped off with water, the residue made basic with saturated aqueous K2CO3, and the mixture extracted 3× with 25 ml of CH2Cl2. The extracts were washed with brine, dried, and the solvent evaporated to give a yellow solid that was purified by radial chromatography eluting with 5% ethanol-0.5% NH4OH-CHCl3 to give 0.55 g of (18) as a yellowish solid. Recrystallization from ether gave a white solid, mp 107°-108° C. NMR ppm (CDCl3) 1.0 (3H, t), 1.15 (1H, m), 1.35-1.6 (4H, m), 1.85 (2H, m), 2.25 (1H, m), 2.37 (1H, bs), 2.75 (1H, m), 2.82-3.0 (3H, m), 3.05 (1H, m), 3.95 (1H, s), 4.2 (1H, d), 4.45 (2H, q), 8.0 (1H, d), 8.12 (1H, d). Anal. C15H23N3O2 requires C: 64.96; H: 8.36; N: 15.15%. Found C: 65.21; H: 8.11; N: 15.25%.

Workup

customthe cooled reaction
customThe butanol was azeotroped off with water
extractionthe mixture extracted 3× with 25 ml of CH2Cl2
washThe extracts were washed with brine
customdried
customthe solvent evaporated
customto give a yellow solid
customthat was purified by radial chromatography
washeluting with 5% ethanol-0.5% NH4OH-CHCl3

Sources & evidence

ORD record: ord-4e7383d0b14f4713935b364db6575bf1
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05182283

Reaction notes

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