Ammonia → HCID 18426289, compound

HRID 133582Notes

Reaction equation

HRID 133582 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:27])[CH2:25][NH2:26])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.N>C(Cl)(Cl)Cl>[C:1]([NH:26][CH2:25][C:24]([NH:23][CH:20]1[CH2:19][CH2:18][N:17]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:22][CH2:21]1)=[O:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 17823029HCID 17823029, compound

Product 1

HCID 18426289HCID 18426289, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A chloroform (0.4 mL) solution of benzoyl chloride (0.060 mmol) was added to a chloroform (1.0 mL) solution of 1-benzyl-4-(glycylamino)piperidine (0.050 mmol) and triethylamine (0.070 mmol). The resulting reaction mixture was shaken at room temperature for 12 hours, and an (aminomethyl)polystyrene resin (1.04 mmol/g, 50 mg, 50 mmol) was added to the mixture. The obtained mixture was shaken at room temperature for 12 hours. The resulting reaction mixture was filtered, and the resin was washed with dichloromethane (0.5 mL). The filtrate and washings were combined, and dichloromethane (4 mL) was added. The solution was washed with a 2 M aqueous solution of NaOH (0.5 mL) to provide 4-(N-benzoylglycyl)amino-1-benzylpiperidine (Compd. No. 386) (11.3 mg, 64%). The purity was determined by RPLC/MS (94%). ESI/MS m/e 352.0 (M++H, C21H25N3O2).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe obtained mixture was shaken at room temperature for 12 hours
  3. customThe resulting reaction mixture
  4. filtrationwas filtered
  5. washthe resin was washed with dichloromethane (0.5 mL)
  6. additiondichloromethane (4 mL) was added
  7. washThe solution was washed with a 2 M aqueous solution of NaOH (0.5 mL)

Sources & evidence

ORD record
ord-ae522e74c94b4a21adbc561637e63235
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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