Hydrochloric Acid → N~1~,N~8~-Bis[3-(benzylamino)propyl]octane-1,8-diamine

HRID 1291718Notes

Reaction equation

HRID 1291718 reaction equation
C(NCCCN[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH3:21])C.C(OC(N(CCCN(C(OC(C)(C)C)=O)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43](C(OC(C)(C)C)=O)[CH2:44][CH2:45][CH2:46][N:47](C(OC(C)(C)C)=O)[CH2:48][CH3:49])CC)=O)(C)(C)C.Cl>CO>[C:41]1([CH2:42][NH:43][CH2:44][CH2:45][CH2:46][NH:47][CH2:48][CH2:49][CH2:8][CH2:9][CH2:10][CH2:11][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][NH:15][CH2:14][C:13]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 60826N,N'-Bis(3-(ethylamino)propyl)-1,7-heptanediamineHCID 18920514HCID 18920514, compound

Product 1

HCID 196733N~1~,N~8~-Bis[3-(benzylamino)propyl]octane-1,8-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N'-Bis[3-(ethylamino)propyl]-1,7-heptanediamine Treat 3,7,15,19-tetra(t-butoxycarbonyl)-3,7,15,19-tetraazaheneicosane (1.68 gm, 0.0024 mol) with HCl in methanol (50 ml, 1.0N) and stir overnight. Filter the mixture and recrystallize the title compound from methanol/water (20:80, v/v) to yield 0.5 gm of the title compound. Rf is 0.39 on silica gel plates eluted with 40% ammonia (concentrated) in methanol; mp 322-23° C. with degradation.

Workup

  1. filtrationFilter the mixture
  2. customrecrystallize the title compound from methanol/water (20:80

Sources & evidence

ORD record
ord-b4635fc1ab684ebe9c76fc036240f685
Source dataset
uspto-grants-1998_05
Patent number
US05753714

Reaction notes

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