Ammonia → HCID 18426168, compound

HRID 133585Notes

Reaction equation

HRID 133585 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:17]1)=[O:13].C(N(CC)CC)C.N>C(Cl)(Cl)Cl>[C:1]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:17]1)=[O:13])(=[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 69216161HCID 69216161, compound

Product 1

HCID 18426168HCID 18426168, 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 3-[(glycylamino)methyl]-1-(4-chlorobenzyl)piperidine (0.050 mmol) and triethylamine (0.070 mmol). The resulting reaction mixture was shaken at room temperature for 2.5 hours, and an (aminomethyl)polystyrene resin (1.04 mmol/g, 50 mg, 50 mmol) was then added to the obtained mixture. The resulting mixture was shaken at room temperature for 12 hours and filtered, and the resin was washed with dichloromethane (0.5 mL). The filtrate and washings were combined, and dichloromethane (4 mL) was added. The obtained mixture was washed with an 2 M aqueous solution of NaOH (0.5 mL) and concentrated to thereby afford 3-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine (Compd. No. 434) -(14.7 mg, 74%). The purity was determined by RPLC/MS (91%). ESI/MS m/e 400 (M++H, C22H26ClN3O2).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe resulting mixture was shaken at room temperature for 12 hours
  3. filtrationfiltered
  4. washthe resin was washed with dichloromethane (0.5 mL)
  5. additiondichloromethane (4 mL) was added
  6. washThe obtained mixture was washed with an 2 M aqueous solution of NaOH (0.5 mL)
  7. concentrationconcentrated to thereby afford 3-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine (Compd. No

Sources & evidence

ORD record
ord-e4b690de20f746ab8a8bd56a99dfd6ac
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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