2,2-Dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal semicarbazone → 2,2,12-Trimethyltridecane-1,11-diamine
Reaction equation
CC(C)(CC=[CH:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14](C(C)C)[NH2:15])C=NO.C1(NN)C=CC=CC=1.[CH3:28][C:29]([CH3:45])([CH2:32][CH:33]=[CH:34][CH2:35][CH2:36][CH:37]=[CH:38][CH2:39][CH:40]([CH:42]([CH3:44])[CH3:43])[NH2:41])[CH:30]=[O:31].[CH3:46][C:47]([CH3:67])([CH2:54][CH:55]=[CH:56][CH2:57][CH2:58][CH:59]=[CH:60][CH2:61][CH:62]([CH:64]([CH3:66])[CH3:65])[NH2:63])[CH:48]=[N:49]NC(N)=O>>[CH3:28][C:29]([CH3:45])([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]([CH:42]([CH3:43])[CH3:44])[NH2:41])[CH:30]=[O:31].[CH2:14]([NH2:15])[C:13]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[CH:64]([CH:62]([NH2:63])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][C:47]([CH3:46])([CH3:67])[CH2:48][NH2:49])([CH3:66])[CH3:65]Participants
Reactant 3
Product 2
Procedure
When the above example is repeated using, in place of 2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal oxime, 34.1 g (0.1 mol) of 2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal phenylhydrazine (prepared according to Example 24), 42 g (0.084 mol) of di-(2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal) hydrazone (prepared according to Example 25), 26.5 g (0.086 mol) of 2,2-dimethyl-11-isopropyl-11-amino-undeca-4,8-dienal semicarbazone (prepared according to Example 26) or . . . 2,2-dimethyl-11-isopropyl-11-amino-undecanal-benzylamine (prepared according to Example 27), 1-isopropyl-10,10-dimethyl-1,11-diamino-undecane is obtained in a yield of 76% of theory, 60.6% of theory, 62.6% of theory and 72% of theory respectively.
Sources & evidence
- ORD record
- ord-0226ec8fdf504c5d856b5302e55b8cab
- Source dataset
- uspto-grants-1982_10
- Patent number
- US04355177
Reaction notes
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