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Trifluoroacetic acid → 4-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidine

HRID 258285
Notes
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Reaction equation

HRID 258285 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=[O:35].[OH-].[Na+]>C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:35])[CH2:10][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57094261HCID 57094261, compound

Product 1

HCID 572905474-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of t-butyl-N-(1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)carbamate produced in Example 1b (1.24 g, 2.74 mmol) in methylene chloride (15 mL) was added trifluoroacetic acid (2.11 mL, 27.37 mmol). After stirring the resulting mixture for 18 h, the reaction was concentrated to give a pale pink syrup. The syrup was dissolved in methylene chloride (100 mL), cooled to 0 C. (ice bath) and treated with 3N sodium hydroxide and extracted with methylene chloride (3×50 mL). The combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL), dried (sodium sulfate), filtered, and concentrated to give the title compound as a white foamy glass (967 mg, 100%); mp 93°-5° C.; MS(CI): 353 (M+H); NMR (300 MHz,DMSO-d6): 1.23(br m, 2H), 1.67-1.85(br m, 2H), 2.71-3.02(br m, 5H), 3.27-3.39(br m, part. submerged, 2H), 3.66(br s, 1H), 4.42(s, 1H), 4.47(s, 1H), 7.00(m, 3H), 7.30-7.66(br m, 4H).

Workup

  1. concentrationthe reaction was concentrated
  2. customto give a pale pink syrup
  3. temperaturecooled to 0 C
  4. extractionextracted with methylene chloride (3×50 mL)
  5. washThe combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-329d108a05ed4022b81a9c0fcaedfc0f
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05266570

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes