1-Naphthoic acid → (2R*,4S*)-2-benzyl-1-(1-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

HRID 264619Notes

Reaction equation

HRID 264619 reaction equation
ClC(N(C)C)=C(C)C.[C:9]1([C:19]([OH:21])=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[CH2:22]([C@@H:29]1[CH2:34][C@@H:33]([N:35]([CH2:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:46]=[CH:45][CH:44]=2)[C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])[CH2:32][CH2:31][NH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH2:22]([C@@H:29]1[CH2:34][C@@H:33]([N:35]([CH2:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:46]=[CH:45][CH:44]=2)[C:36](=[O:41])[C:37]([F:39])([F:40])[F:38])[CH2:32][CH2:31][N:30]1[C:19]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:21])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 68471-Naphthoic acidHCID 8471TriethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57312928(2R*,4S*)-2-benzyl-1-(1-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

92 μl (0.655 mmol) of 1-chloro-N,N,2-trimethyl-1-propen-1-amine are added to a solution of 96 mg (0.561 mmol) of 1-naphthoic acid in 2 ml of dry, methylene chloride at 0°, and the mixture is stirred at 0° for 1 hour and at room temperature for 1 hour. Subsequently a solution of 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine and 130 μl (0.936 mmol) of triethylamine in 3 ml of methylene chloride is added dropwise over the course of 10 minutes to this yellow solution at room temperature. After stirring at room temperature for 3 hours, water is added, the organic phase is separated off and washed twice more with water. The organic phases are dried over magnesium sulfate and evaporated to dryness. The yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (800:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.49, FD-MS: M+ =581.

Workup

  1. customof dry
  2. stirringAfter stirring at room temperature for 3 hours
  3. customthe organic phase is separated off
  4. washwashed twice more with water
  5. dry with materialThe organic phases are dried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-2c1b241613544f11b45f42c18b1fca6c
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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