Triethylamine → 558446-23-4

HRID 899683Notes

Reaction equation

HRID 899683 reaction equation
[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:24][C:25]([O:28][C:29](ON=C(C1C=CC=CC=1)C#N)=[O:30])([CH3:27])[CH3:26]>O1CCCC1>[C:25]([O:28][C:29](=[O:30])[NH:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 68954262N-(5,6,7,8-Tetrahydro-quinolin-8-yl)-butane-1,4-diamine

Product 1

HCID 42609132558446-23-4Yield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (6.77 g, 30.9 mmol) in tetrahydrofuran (155 ml) was added slowly triethylamine (4.30 ml, 30.9 mmol) and Boc-ON (7.60 g, 30.9 mmol). The mixture was stirred for 72 hours at room temperature under a N2 atmosphere. The mixture was concentrated and purified by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v). A second purification by column chromatography on silica gel (ethyl acetate) afforded the product as a brown oil (8.03 g, 80%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.60 (s, 4H), 1.78 (m, 2H), 1.99 (m, 2H), 2.78 (m, 5H), 3.15 (m, 2H), 3.77 (t, 1H), 4.87 (s, 1H), 7.07 (dd, 1H, J=7.45, 4.82 Hz), 7.83 (d, 1H, J=7.89 Hz), 8.38 (d, 1H, J=4.38 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v)
  3. customA second purification by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-406c931d3e3c430f969f825bfef60864
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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