Hydrochloric Acid → HCID 69028887, compound

HRID 489595Notes

Reaction equation

HRID 489595 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:44])[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:31]=3)[CH2:25][CH2:24]2)[CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:45]>CO>[ClH:45].[C:38]1([C:37]#[C:36][C:32]2[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=2)[C:29]([N:26]2[CH2:25][CH2:24][CH:23]([C:19]3[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=3)[CH2:16][NH2:8])[CH2:28][CH2:27]2)=[O:44])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69028940HCID 69028940, compound

Product 1

HCID 69028887HCID 69028887, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N,N-Bis-(tert-butoxycarbonyl)-3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylamine (100 mg, 0.17 mmol) in methanol (10 ml), cooled to 0° C., was saturated with hydrogen chloride gas. The mixture was stirred at ambient temperature for 4 hours then concentrated to dryness under vacuum. The residue was triturated with a mixture of dichloromethane and diethyl ether to give 3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylamine hydrochloride as a white amorphous solid (46 mg). 1H NMR [(CD3)2SO, 500 MHz]: δ 7.61-7.30 (m, 13H), 4.62 (br m, 1H), 4.00 (s, 2H), 3.62 (br m, 1H), 3.25 (br m, 1H), 2.85 (br m, 2H), 1.88 (br m, 1H), 1.70 (br m, 3H). MS(EI): 395(M++H).

Workup

  1. concentrationthen concentrated to dryness under vacuum
  2. customThe residue was triturated with a mixture of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-b9702193f5034becabe47016fa04a15a
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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