N-Methylcyclohexylamine → HCID 13987626, compound

HRID 256189Notes

Reaction equation

HRID 256189 reaction equation
[O:1]=[C:2]1[NH:23][C:5]2=[N:6][C:7]3[CH:8]=[CH:9][C:10]([N:14]4[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]4)=[CH:11][C:12]=3[CH:13]=[C:4]2[NH:3]1.[CH:24]1([NH:30][CH3:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(Cl)Cl>[CH:24]1([N:30]([CH3:31])[C:20]([CH:17]2[CH2:18][CH2:19][N:14]([C:10]3[CH:9]=[CH:8][C:7]4[N:6]=[C:5]5[NH:23][C:2](=[O:1])[NH:3][C:4]5=[CH:13][C:12]=4[CH:11]=3)[CH2:15][CH2:16]2)=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 13987621HCID 13987621, compound

Product 1

HCID 13987626HCID 13987626, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A stirred mixture of 1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-4-piperidinecarboxylic acid (3.12 g, 10 mmol) and N-cyclohexyl-N-methylamine (1.36 g, 12 mmol) were combined in dimethylformamide (200 mL) and cooled to -20° C. Triethylamine (2.91 mL, 21 mmol) and diphenylphosphoryl azide (2.59 mL, 12 mmol) were added, the mixture stirred at -20° C. for 3 hours, and allowed to warm to room temperature. After 18 hours, the mixture was diluted with CH2Cl2 (200 mL), scratched to initiate crystallization, and stirred for an additional 72 hours. The resultant precipitate was collected, washed with CH2Cl2, and dried to give 2.09 g of a pale yellow solid (51%). Crystallization from dimethylformamide (80 mL) gave 1.02 g of pale yellow crystals, m.p. 318°-321° C.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 18 hours
  3. customcrystallization
  4. stirringstirred for an additional 72 hours
  5. customThe resultant precipitate was collected
  6. washwashed with CH2Cl2
  7. customdried

Sources & evidence

ORD record
ord-c292b2e576624cdfbb802080a8692ef9
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Reaction notes

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